Formic Acid → N-[5-[2-(3-methoxyphenyl)ethyl]-1H-pyrazol-3-yl]-4-(4-methylsulfonylpiperazin-1-yl)benzamide

HRID 16786Notes

Reaction equation

HRID 16786 reaction equation
C(O)=O.C([N:8]1[C:12]([NH:13][C:14](=[O:31])[C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][N:24]([S:27]([CH3:30])(=[O:29])=[O:28])[CH2:23][CH2:22]3)=[CH:17][CH:16]=2)=[CH:11][C:10]([CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([O:40][CH3:41])[CH:35]=2)=[N:9]1)(C)(C)C>>[CH3:41][O:40][C:36]1[CH:35]=[C:34]([CH2:33][CH2:32][C:10]2[NH:9][N:8]=[C:12]([NH:13][C:14](=[O:31])[C:15]3[CH:16]=[CH:17][C:18]([N:21]4[CH2:26][CH2:25][N:24]([S:27]([CH3:30])(=[O:28])=[O:29])[CH2:23][CH2:22]4)=[CH:19][CH:20]=3)[CH:11]=2)[CH:39]=[CH:38][CH:37]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 66589934N-(1-tert-butyl-3-(3-methoxyphenethyl)-1H-pyrazol-5-yl)-4-(4-(methylsulfonyl)piperazin-1-yl)benzamide

Product 1

HCID 66589820N-[5-[2-(3-methoxyphenyl)ethyl]-1H-pyrazol-3-yl]-4-(4-methylsulfonylpiperazin-1-yl)benzamideYield 18.9%

Procedure

A solution of formic acid (5 mL, 130.36 mmol) and N-(1-tert-butyl-3-(3-methoxyphenethyl)-1H-pyrazol-5-yl)-4-(4-(methylsulfonyl)piperazin-1-yl)benzamide (255 mg, 0.47 mmol) was stirred at 85° C. for 2 h. The reaction mixture was cooled and evaporated to dryness. The crude product was purified by reverse phase prep. HPLC (basic) using a 36-46% gradient of acetonitrile in water, containing 1% 0.880 ammonia. The clean fractions were combined and evaporated to afford the title compound (43.0 mg, 18.82%) as a white solid; 1H NMR (499.9 MHz, DMSOd6+CD3CO2D) δ 2.87 (3H, s), 2.88-2.92 (4H, m), 3.28-3.32 (4H, m), 3.39-3.42 (4H, m), 3.73 (3H, s), 6.30 (1H, s), 6.71-6.74 (1H, m), 6.77 (1H, s0, 6.80 (2H, d), 6.94-6.98 (2H, m), 7.16 (1H, t), 7.85-7.89 (2H, m).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customevaporated to dryness
  3. customThe crude product was purified by reverse phase prep
  4. additioncontaining 1% 0.880 ammonia
  5. customevaporated

Sources & evidence

ORD record
ord-b01fae78817149ecafa7d35b9afe8e0e
Source dataset
uspto-grants-2010_06
Patent number
US07737149B2

Reaction notes

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