Water → HCID 69313156, compound

HRID 271520Notes

Reaction equation

HRID 271520 reaction equation
CS[C:3]1[N:8]=[C:7]([C:9]2[O:10][C:11]([CH2:24][N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:12][C:13]=2[C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[C:19](=[O:23])[CH2:18][CH2:17]3)[CH:6]=[CH:5][N:4]=1.O>[Ni].C(O)C>[N:25]1([CH2:24][C:11]2[O:10][C:9]([C:7]3[CH:6]=[CH:5][N:4]=[CH:3][N:8]=3)=[C:13]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[C:19](=[O:23])[CH2:18][CH2:17]4)[CH:12]=2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

5

Reactant 2

HCID 962WaterHCID 69314810HCID 69314810, compound

Product 1

HCID 69313156HCID 69313156, compoundYield 104.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of the product of Step 4 (0.135 g, 0.329 mmol) and Raney nickel (0.262 g of an aqueous suspension) in ethanol (15 ml) and water (5 ml) was heated at 100° C. for 20 hours. The mixture was then cooled to room temperature, filtered through celite and the filtrate reduced in vacuo. The residue was then purified by chromatography on silica gel eluting with a mixture of 0.880 ammonia/methanol/dichloromethane (0.5:4.5:95), to furnish the title compound (0.016 g, 0.345 mmol); MS(ES+) m/e 374 [M+H]+.

Workup

  1. filtrationfiltered through celite
  2. customThe residue was then purified by chromatography on silica gel eluting with a mixture of 0.880 ammonia/methanol/dichloromethane (0.5:4.5:95)

Sources & evidence

ORD record
ord-7c0d76c17f0d4d0094df899cbccd761c
Source dataset
uspto-grants-2008_11
Patent number
US07452906B2

Reaction notes

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