Reaction SMILES: [N:1]1([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:15][N:16]([CH2:59][CH:60]=O)[C:17](=[O:58])[C:18]1[CH:57]=[CH:56][CH:55]=[C:20]([C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([N:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:26][C:25]=2[C:36]2[CH:41]=[C:40]([C:42](=[O:54])[NH:43][C@@H:44]3[C:53]4[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=4)[CH2:47][CH2:46][CH2:45]3)[CH:39]=[CH:38][N:37]=2)=[O:22])[CH:19]=1.C(O)(=O)C.[BH3-]C#N.[Na+]>C(O)C>[CH3:15][N:16]([CH2:59][CH2:60][N:4]1[CH2:5][CH2:6][CH2:7][N:1]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:2][CH2:3]1)[C:17](=[O:58])[C:18]1[CH:57]=[CH:56][CH:55]=[C:20]([C:21](=[O:22])[NH:23][C:24]2[CH:29]=[CH:28][C:27]([N:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:26][C:25]=2[C:36]2[CH:41]=[C:40]([C:42](=[O:54])[NH:43][C@@H:44]3[C:53]4[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=4)[CH2:47][CH2:46][CH2:45]3)[CH:39]=[CH:38][N:37]=2)[CH:19]=1
Reactant: CC(C)(C)OC(=O)N1CCCNCC1
Reactant: CN(CC=O)C(=O)c1cccc(C(=O)Nc2ccc(N3CCCCC3)cc2-c2cc(C(=O)N[C@H]3CCCc4ccccc43)ccn2)c1
Agent: [BH3-]C#N
Agent: [Na+]
Solvent: CCO
Solvent: CC(=O)O
Product: CN(CCN1CCCN(C(=O)OC(C)(C)C)CC1)C(=O)c1cccc(C(=O)Nc2ccc(N3CCCCC3)cc2-c2cc(C(=O)N[C@H]3CCCc4ccccc43)ccn2)c1
Temperature: 25 °C
Reaction time: 0.5 h

Procedure:
This compound was prepared according to the procedure described for the synthesis of Example 187 using tert-butyl 1,4-diazepane-1-carboxylate in place of L-proline-tert-butyl ester. Into a 50-mL round-bottom flask, was placed a solution of (S)—N1-methyl-N1-(2-oxoethyl)-N3-(4-(piperidin-1-yl)-2-(4-(1,2,3,4-tetrahydronaphthalen-1-ylcarbamoyl)pyridin-2-yl)phenyl)isophthalamide (100 mg, 0.16 mmol, 1.00 equiv) in ethanol (5 mL), tert-butyl 1,4-diazepane-1-carboxylate (50 mg, 0.25 mmol, 1.57 equiv), acetic acid (20 mg, 0.33 mmol, 2.10 equiv). The resulting solution was stirred for 0.5 h at room temperature. To the above was added NaBH3CN (20 mg, 0.32 mmol, 2.00 equiv). The resulting solution was allowed to react, with stirring, for an additional 3 h at room temperature. The resulting mixture was concentrated under vacuum. The pH value of the solution was adjusted to 8-9 with sodium bicarbonate. The resulting solution was extracted with 3×20 mL of ethyl acetate and the organic layers combined. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product (100 mg) was purified by Prep-HPLC with the following conditions (1#-Waters 2767-3): Column, SunFire Prep C18, 19*150 mm 5 um; mobile phase, water with 0.05% TFA and CH3CN (25% CH3CN up to 43% in 6 min); Detector, Waters2545 UvDector 254&270 nm. 60.2 mg product was obtained. This resulted in 60.2 mg (47%) of (S)-tert-butyl 4-(2-(N-methyl-3-(4-(piperidin-1-yl)-2-(4-(1,2,3,4-tetrahydronaphthalen-1-ylcarbamoyl)pyridin-2-yl)phenylcarbamoyl)benzamido)ethyl)-1,4-diazepane-1-carboxylate as a light yellow solid. LC-MS (ES, m/z): 814 [M+H]+ H-NMR (300 MHz, DMSO, ppm): 12.23 (s, 1H), 9.38 (s, 1H), 9.18 (d, J=8.4 Hz, 1H), 8.88 (d, J=5.1 Hz, 1H), 8.31 (s, 1H), 8.23 (d, J=7.8 Hz, 1H), 7.98 (d, J=6.3 Hz, 2H), 7.85 (d, J=5.1 Hz, 1H), 7.68-7.56 (m, 3H), 7.28-7.12 (m, 5H), 5.25 (d, J=6.0 Hz, 1H), 3.82-3.46 (m, 12H), 3.30 (s, 3H), 2.96-2.51 (m, 2H), 2.07-1.99 (m, 4H), 1.83-1.72 (m, 6H), 1.59 (d, J=4.2 Hz, 1H), 1.42 (s, 9H).