Ammonia → HCID 22479693, compound

HRID 1349625Notes

Reaction equation

HRID 1349625 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([NH:15][CH2:16][CH2:17][CH2:18][C:19]([O:21]C)=O)=[O:14])=[CH:10][CH:11]=2)[C:6]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[N:5]1)(=O)C.[NH3:30]>CO>[C:19]([CH2:18][CH2:17][CH2:16][NH:15][C:13]([C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[NH:4][N:5]=[C:6]2[C:23]1[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=1)=[O:14])(=[O:21])[NH2:30]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 22479900HCID 22479900, compound

Product 1

HCID 22479693HCID 22479693, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A sealed glass bomb containing methyl 4-{[1-acetyl-3-(4-fluorophenyl)-1H-indazole-5-yl]carbonylamino}butanoate (95 mg, 0.239 mmol) in methanol with saturated ammonia (7 mL) was heated to 80° C. for 18 hours. The reaction mixture was condensed and the resulting solid was purified by HPLC to afford the title compound (35 mg, 43% yield). 1H NMR (DMSO-d6) δ 13.43 (br s, 1H), 8.50 (s, 1H), 8.04 (m, 2H), 7.87 (d, 1H), 7.58 (d, 1H), 7.37 (t, 1H), 7.29 (s, 1H), 6.75 (br s, 1H), 3.75 (m, 2H), 2.09 (t, 2H), 1.73 (t, 2H); ES-MS (m/z) 341 [M+1]+.

Workup

  1. customcondensed
  2. customthe resulting solid was purified by HPLC

Sources & evidence

ORD record
ord-91b0b0431a684b4eb5f65471f9d73ab2
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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