Reaction SMILES: [OH:1][CH:2]1[CH2:3][CH:4]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:5][CH2:6][C:7]([C:9]2[N:13]([CH3:14])[N:12]=[CH:11][C:10]=2[N+:15]([O-])=O)=[CH:8]1>CO.[Pd]>[NH2:15][C:10]1[CH:11]=[N:12][N:13]([CH3:14])[C:9]=1[CH:7]1[CH2:6][CH2:5][CH:4]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:3][CH:2]([OH:1])[CH2:8]1
Reactant: Cn1ncc([N+](=O)[O-])c1C1=CC(O)CC(NC(=O)OC(C)(C)C)CC1
Agent: [Pd]
Solvent: CO
Product: Cn1ncc(N)c1C1CCC(NC(=O)OC(C)(C)C)CC(O)C1

Procedure:
A solution of (E)-tert-butyl 3-hydroxy-5-(1-methyl-4-nitro-1H-pyrazol-5-yl)cyclohept-4-enylcarbamate (620 mg, 1.76 mmol) in MeOH (40 mL) was passed through the H-Cube® (full H2, 70° C., flow rate: 1 mL/min, 30 mm 10% Pd/C cartridge). The solvent was removed under reduced pressure to afford tert-butyl 5-(4-amino-1-methyl-1H-pyrazol-5-yl)-3-hydroxycycloheptylcarbamate as a yellow oil. To a solution of this amine in DCM (50 mL) was added DIPEA (0.92 mL, 5.28 mmol), PyBOP (1.37 g, 2.64 mmol) and 5-(tert-butoxycarbonylamino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acid (690 mg, 1.94 mmol) and the mixture was stirred at room temperature for 18 hr. The mixture was diluted with DCM (100 mL) and washed with water (50 mL). The organic layer was separated, dried over MgSO4 and the solvent removed under reduced pressure. Purification via silica gel column chromatography (75% EtOAc/isohexane) gave tert-butyl (5-(4-(5-tert-butoxycarbonylamino-2-(2,6-difluorophenyl)thiazole-4-carboxamido)-1-methyl-1H-pyrazol-5-yl)-3-hydroxycycloheptylcarbamate as a yellow foam (890 mg). This foam (890 mg, 1.34 mmol) was dissolved in DCM (50 mL) and Dess-Martin periodinane (684 mg, 1.61 mmol) was added, the mixture was stirred at room temperature for 1.5 hr. The mixture was quenched with a 1/1 aqueous solution of 20% sodium thiosulfate/saturated aqueous NaHCO3 (100 mL), layers extracted, dried over MgSO4 and the solvent removed under reduced pressure. Purification via silica gel column chromatography (0-100% EtOAc/isohexane) gave a light yellow solid (500 mg). A portion of this solid (356 mg, 0.54 mmol) was dissolved in dry THF (5 mL) and cooled at 0° C. before a solution of methylmagnesium bromide (3 M in Et2O, 0.72 mL, 2.15 mmol) was added dropwise. The mixture was stirred at 0° C. for 3 hr, before an additional amount of methylmagnesium bromide (3 M in Et2O, 0.3 mL, 0.9 mmol) was added. The mixture was stirred for a further 6 hr, quenched with a saturated solution of ammonium chloride (30 mL), extracted with EtOAc (50 mL) and washed with water. The combined organic layers were dried over MgSO4 and the solvent removed under reduced pressure. Purification via silica gel column chromatography (0-100% EtOAc/isohexane) gave a light yellow oil. The four diastereomers obtained were separated by preparative HPLC to give Diastereomer 1 as a white solid (22 mg, 2% over five steps). This solid (22 mg, 0.03 mmol) was dissolved in HCl in dioxane (4 M, 1 mL, 4.0 mmol) and MeOH (1 mL) and was stirred at room temperature for 5 hr. The solvents were removed under reduced pressure and the crude residue was purified by preparative HPLC to give 456 as an orange solid (15 mg, 96%). 1H NMR (400 MHz, d6-DMSO) δ 8.79 (s, 1H), 8.45 (s, 2H), 7.59-7.50 (m, 2H), 7.33-7.25 (m, 2H), 3.78 (s, 3H), 3.58-3.05 (m, 1H), 3.17 (s, 1H), 2.85-2.77 (m, 1H), 2.08-1.92 (m, 4H), 1.88-1.78 (m, 5H), 1.55-1.44 (m, 1H), 1.17 (s, 3H). LCMS (ES+) m/z 477 (M+1)