HCID 178465767, compound → HCID 178465766, compound

HRID 1349596Notes

Reaction equation

HRID 1349596 reaction equation
[C:1]([C:4]1([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:20]([C:22]4[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][CH:23]=4)=[O:21])[CH:17]=3)[NH:12][N:11]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH2:5]1)(=[O:3])[CH3:2]>[Pd].C(OCC)(=O)C>[C:1]([C:4]1([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:20]([C:22]4[CH:23]=[CH:24][C:25]([NH2:28])=[CH:26][CH:27]=4)=[O:21])[CH:17]=3)[NH:12][N:11]=2)[CH:5]=[CH:6][CH:7]=[CH:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 178465767HCID 178465767, compound

Product 1

HCID 178465766HCID 178465766, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of N-(1-acetyl-3-phenyl(1H-indazol-5-yl))(4-nitrophenyl)carboxamide (246 mg, 0.710 mmol) and palladium on activated carbon (10%, 57 mg) in ethyl acetate (30 mL) was stirred under hydrogen atmosphere at room temperature for 18 hours. The reaction mixture was filtered through celite and combined with ethyl acetate washings. The filtrate was concentrated to give the title compound (246 mg, 94% yield). 1H NMR (DMSO-d6) δ 10.04 (s, 1H), 8.61 (s, 1H) 8.31 (d, 1H), 7.99 (m, 2H), 7.64 (m, 4H), 6.58 (d, 2H), 5.78 (s, 2H), 2.76 (s, 3H); ES-MS (m/z) 371 [M+1]+.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-6060a7b23d534610bbb6d6d51ffc401b
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

Loading…