Water → HCID 21948896, compound

HRID 2215474Notes

Reaction equation

HRID 2215474 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]([CH3:19])([CH3:18])[CH2:10][CH:11]([C:14]([F:17])([F:16])[F:15])[CH:12]=O.[NH2:20][C:21]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:22]=1[CH:23]=[CH:24][C:25]([CH3:31])=[N:26]2.[OH2:32].[BH4-].[Na+]>C1(C)C=CC=CC=1.C(O)(=O)C.CCCCCC.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]([CH3:19])([CH3:18])[CH2:10][C:11]([C:14]([F:17])([F:16])[F:15])([OH:32])[CH2:12][NH:20][C:21]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:22]=1[CH:23]=[CH:24][C:25]([CH3:31])=[N:26]2

Participants

8

Reactant 4

HCID 962WaterHCID 1486835-Quinolinamine, 2-methyl-HCID 4311764Sodium borohydrideHCID 21948930HCID 21948930, compound

Product 1

HCID 21948896HCID 21948896, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 1140TolueneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

175 mg (0.62 mmol) of 4-(2,5-difluorophenyl)-4-methyl-2-(trifluoromethyl)-pentanal and 125 mg (0.78 mmol) of 5-amino-2-methylquinoline are stirred in 10 ml of toluene and 3 ml of acetic acid for 18 hours at room temperature and refluxed for another 2 hours in a water separator. The crude product is reduced analogously to 79 with 120 mg (3.16 mmol) of NaBH4 in 5 ml of acetic acid. After chromatography on silica gel with hexane-ethyl acetate (30%), 45 mg of product is obtained.

Sources & evidence

ORD record
ord-c08b0b0c1d814347a5447cf41df42e9b
Source dataset
uspto-grants-2006_09
Patent number
US07109212B2

Reaction notes

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