HCID 178465767, compound → HCID 178465766, compound

HRID 1353663Notes

Reaction equation

HRID 1353663 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-1aa9a0985ca24cc79180ae9d4d84960a
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

Loading…