Ammonia methanol → HCID 58851426, compound

HRID 1696603Notes

Reaction equation

HRID 1696603 reaction equation
C(O[C:4](=[O:35])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]([NH:17][C:18]([NH:20][C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][CH:22]=3)=[O:19])=[CH:15][C:14]([C:31]([CH3:34])([CH3:33])[CH3:32])=[N:13]2)=[CH:8][CH:7]=1)C.[NH3:36].CO>CO>[C:31]([C:14]1[CH:15]=[C:16]([NH:17][C:18]([NH:20][C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=[CH:23][CH:22]=2)=[O:19])[N:12]([C:9]2[CH:8]=[CH:7][C:6]([CH2:5][C:4]([NH2:36])=[O:35])=[CH:11][CH:10]=2)[N:13]=1)([CH3:34])([CH3:33])[CH3:32]

Participants

4

Reactant 2

HCID 21705897Ammonia methanolHCID 58011008HCID 58011008, compound

Product 1

HCID 58851426HCID 58851426, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of {4-[3-t-butyl-5-(3-naphthalen-1-yl-ureido)pyrazol-1-yl]phenyl}acetic acid ethyl ester (150 mg, 0.32 mmol, intermediate in Example 559) in MeOH (2 mL) was added NH3/MeOH (10 mL) at RT. The mixture was stirred at that temperature overnight. After removal of the solvent, the crude product was purified by preparative HPLC to afford 2-{4-[3-t-butyl-5-(3-naphthalen-1-ylureido)pyrazol-1-yl]phenyl}acetamide (48 mg, 31% yield). 1H NMR (300 MHz, CD3OD): δ 7.87 (m, 2H), 7.76 (d, J=5.4 Hz, 1H), 7.68 (d, J=6.0 Hz, 1H), 7.53-7.42 (m, 7H), 6.57 (s, 1H), 3.64 (s, 2H), 1.36 (s, 9H); MS (ESI) m/z: 442 (M+H+).

Workup

  1. customAfter removal of the solvent
  2. customthe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-c1c0799b6a564f08a27bcaa2c1eedfff
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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