Reaction SMILES: C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[CH:15]=2)[CH:10]=[C:9]1[C:27]1[C:28]2[S:41][C:40]([CH2:42]OS(C)(=O)=O)=[CH:39][C:29]=2[N:30](C(OC(C)(C)C)=O)[N:31]=1)=O)(C)(C)C.C(N(CC)CC)C.[OH:55][CH:56]1[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]1>ClCCl>[N:21]1([CH2:20][CH2:19][CH2:18][O:17][C:14]2[CH:15]=[C:16]3[C:11]([CH:10]=[C:9]([C:27]4[C:28]5[S:41][C:40]([CH2:42][N:59]6[CH2:60][CH2:61][CH:56]([OH:55])[CH2:57][CH2:58]6)=[CH:39][C:29]=5[NH:30][N:31]=4)[NH:8]3)=[CH:12][CH:13]=2)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1
Reactant: OC1CCNCC1
Reactant: CC(C)(C)OC(=O)n1nc(-c2cc3ccc(OCCCN4CCCCC4)cc3n2C(=O)OC(C)(C)C)c2sc(COS(C)(=O)=O)cc21
Solvent: CCN(CC)CC
Solvent: ClCCl
Product: OC1CCN(Cc2cc3[nH]nc(-c4cc5ccc(OCCCN6CCCCC6)cc5[nH]4)c3s2)CC1
Temperature: 45 °C
Reaction time: 15 h
Yield: 14.8 %

Procedure:
To 6-(3-bromo-propoxy)-2-(1-tert-butoxycarbonyl-5-hydroxymethyl-1H-thieno[3,2-c]pyrazol-3-yl)-indole-1-carboxylic acid tert-butyl ester [990 mg, 1.63 mmol, Intermediate (77)] in acetonitrile (20 mL) were added polymer supported DIEA (3.83 mmol/g, 850 mg, 3.26 mmol) and piperidine (0.32 mL, 3.26 mmol). The mixture was stirred gently at 60° C. for 4 hours. The PS-DIEA was filtered and the solvent was removed. The residue was chromatographed through silica gel (dichloromethane/1.0M ammonia in methanol, 95/05) to produce 2-(1-tert-butoxycarbonyl-5-hydroxymethyl-1H-thieno[3,2-c]pyrazol-3-yl)-6-(3-piperidin-1-yl-propoxy)-indole-1-carboxylic acid tert-butyl ester [730 mg, 74%, Intermediate (78)] as a white foam. LC/MS: 611.2 (M+H), RT=3.05 minutes. Step 2. To 2-(1-tert-butoxycarbonyl-5-hydroxymethyl-1H-thieno[3,2-c]pyrazol-3-yl)-6-(3-piperidin-1-yl-propoxy)-indole-1-carboxylic acid tert-butyl ester [1.21 g, 1.98 mmol, Intermediate (78)] in dichloromethane (25 mL) at 0° C. was added triethylamine (0.29 mL, 2.28 mmol) and methane sulfonyl chloride (0.34 mL, 4.40 mmol). The mixture was stirred at 0° C. for 30 minutes then at room temperature for 4 hours. It was diluted with dichloromethane then washed with saturated sodium bicarbonate. The organic layer was dried over magnesium sulfate and concentrated. The residue was chromatographed through silica gel (dichloromethane/methanol, 90/10 as eluant) to produce 2-(1-tert-butoxycarbonyl-5-methanesulfonyloxymethyl-1H-thieno [3,2-c]pyrazol-3-yl)-6-(3-piperidin-1-yl-propoxy)-indole-1-carboxylic acid tert-butyl ester [0.85 g, 62%, Intermediate (79)] as a yellow foam. LC/MS: 689.3 (M+H), RT=2.58 minutes. Step 3. To 2-(1-tert-butoxycarbonyl-5-methanesulfonyloxymethyl-1H-thieno[3,2-c]pyrazol-3-yl)-6-(3-piperidin-1-yl-propoxy)-indole-1-carboxylic acid tert-butyl ester [150 mg, 0.26 mmol, Intermediate (79)] in dichloromethane (5 mL) were added triethylamine (40 μL, 0.31 mmol), and 4-hydroxypiperidine (55 mg, 0.52 mmol). The mixture was stirred at 45° C. for 15 hours. It was concentrated. The residue was chromatographed through silica gel (dichloromethane/1.0M ammonia in methanol, 90/10). The appropriate fractions were combined and concentrated. The residue was dissolved into dichloromethane (2 mL) and anisole (0.5 mL). Trifluoroacetic acid (0.5 mL) was added. The solution was stirred at 45° C. for 3 hours. It was then directly loaded onto a cationic ion exchange column (Varian Mega Bond Elut SCX, 5 g) washed with methanol and eluted with 1.0M ammonia in methanol. The appropriate fractions were combined and concentrated. The residue was triturated in dichloromethane then chromatographed through silica gel (dichloromethane/methanol, 90/10 as eluant) to provide 1-{3-[6-(3-piperidin-1-yl-propoxy)-1H-indol-2-yl]-1H-thieno[3,2-c]pyrazol-5-ylmethyl}-piperidin-4-ol [19 mg, Example 63]. LC/MS: 494.3 (M+H), RT=1.77 minutes; 1H NMR [300 Mhz, (CD3)2SO]: δ 13.01 (s, 1h), 11.30 (s, 1H), 7.40 (d, J=8.5 Hz, 1H), 7.04 (s, 1H), 6.90 (s, 1H), 6.64 (dd, J1=8.6 Hz, J2=2.1 Hz, 1H), 4.54 (d, J=4 Hz, 1H), 3.98 (t, J=6.2 Hz, 2H), 3.71 (s, 2H), 3.46 (m, 1H), 2.77 (m, 2H), 2.49-2.35 (m, 6H), 2.15 (t, J=9.7 Hz, 2H), 1.90 (t, J=6.7Hz, 2H), 1.73 (m, 2H), 1.55-1.30 (m, 8H).