Water → HCID 9827187, compound

HRID 1654073Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]1[C:12](=[O:36])[N:13]([CH2:22][C:23]([NH:25][CH:26]([CH:33]([CH3:35])[CH3:34])[CH:27]([OH:32])[C:28]([F:31])([F:30])[F:29])=[O:24])[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:15][C:8]2=1)#N.O.[PH2]([O-])=[O:39].[Na+].O>N1C=CC=CC=1.C(O)(=O)C.[Ni].CO>[CH:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]1[C:12](=[O:36])[N:13]([CH2:22][C:23]([NH:25][CH:26]([CH:33]([CH3:35])[CH3:34])[C:27](=[O:32])[C:28]([F:31])([F:29])[F:30])=[O:24])[C:14]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:15][C:8]2=1)=[O:39]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-(8-cyano-1-oxo-3-phenyl-1,2-dihydropyrido[3,4-b]indol-2-yl)-N-(3,3,3-trifluoro-2-hydroxy-1-isopropylpropyl)acetamide (0.5 g) and sodium hypophosphite hydrate (0.35 g) in pyridine (3 mL), acetic acid (1.5 mL), and H2O (1.5 mL) was added a small amount of Raney nickel (50% slurry in water, pH greater than 9) and the resulting mixture was heated at 60° C. for 1 hour. Additional sodium hypophosphite hydrate (0.1 g) was added and the mixture was heated at 60° C. for 1 hour. The reaction mixture was diluted with methanol, filtered through diatomaceous earth, evaporated, and diluted with ethyl acetate. The resulting solution was washed with 1N hydrochloric acid, dried, and evaporated to give the aldehyde (0.4 g) as a yellow solid; TLC: Rf =0.45, methanol:dichloromethane (5:95);

Workup

temperaturethe mixture was heated at 60° C. for 1 hour
filtrationfiltered through diatomaceous earth
customevaporated
additiondiluted with ethyl acetate
washThe resulting solution was washed with 1N hydrochloric acid
customdried
customevaporated

Sources & evidence

ORD record: ord-62e6f6bde2964d6ca77be4eb222924b1
Source dataset: uspto-grants-1995_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05405852

Reaction notes

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