HCID 86713811, compound → HCID 86713812, compound

HRID 521863Notes

Reaction equation

HRID 521863 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]2[CH2:13][O:12][CH2:11][CH:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:9][CH2:8]2)=[C:5]([N+:22]([O-])=O)[CH:4]=[N:3]1>CO.[Pd]>[NH2:22][C:5]1[CH:4]=[N:3][N:2]([CH3:1])[C:6]=1[CH:7]1[CH2:13][O:12][CH2:11][CH:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:18])[CH3:20])[CH2:9][CH2:8]1

Participants

4

Reactant 1

HCID 86713811HCID 86713811, compound

Product 1

HCID 86713812HCID 86713812, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl N-[6-(2-methyl-4-nitro-pyrazol-3-yl)oxepan-3-yl]carbamate (53 mg, 0.16 mmol) in MeOH (25 mL) was passed through the H-Cube® (50 bar, 50° C., flow rate: 1 mL/min, 30 mm 10% Pd/C cartridge). The solvent was removed under reduced pressure to afford tert-butyl N-[6-(4-amino-2-methyl-pyrazol-3-yl)oxepan-3-yl]carbamate as a brown oil. To a solution of this oil in DCM (5 mL) was added 5-(tert-butoxycarbonylamino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acid (72 mg, 0.20 mmol), PyBOP (133 g, 0.25 mmol) and DIPEA (0.17 mL, 0.94 mmol) and the mixture was stirred at room temperature for 16 hr. The reaction was quenched with water and extracted with EA (3×). The organic layers were combined and the solvent was removed under reduced pressure. Purification via silica gel column chromatography (0-100% EtOAc/heptane) gave tert-butyl N-[6-[4-[[5-(tert-butoxycarbonylamino)-2-(2,6-difluorophenyl)thiazole-4-carbonyl]amino]-2-methyl-pyrazol-3-yl]oxepan-3-yl]carbamate (100 mg, 99%).

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-491ed995f786488b8848cfa140c950fc
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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