5-Quinolinamine, 2-methyl- → HCID 21948842, compound

HRID 2055016Notes

Reaction equation

HRID 2055016 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1([CH2:13][CH:14]([C:17]([F:20])([F:19])[F:18])[CH:15]=O)[CH2:12][CH2:11][CH2:10]1.[NH2:21][C:22]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:23]=1[CH:24]=[CH:25][C:26]([CH3:32])=[N:27]2.[BH4-].[Na+].CCCCCC.C(OCC)(=[O:43])C>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1([CH2:13][C:14]([C:17]([F:20])([F:19])[F:18])([OH:43])[CH2:15][NH:21][C:22]2[CH:31]=[CH:30][CH:29]=[C:28]3[C:23]=2[CH:24]=[CH:25][C:26]([CH3:32])=[N:27]3)[CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 4

HCID 1486835-Quinolinamine, 2-methyl-HCID 4311764Sodium borohydrideHCID 21226206Ethyl acetate hexaneHCID 21948864HCID 21948864, compound

Product 1

HCID 21948842HCID 21948842, compound

Procedure

Analogously to Example 79, 200 mg (0.64 mmol) of 3-[1-(2-chloro-5-fluorophenyl)cyclobut-1-yl]-2-(trifluoromethyl)-propanal and 126 mg (0.80 mmol) of 5-amino-2-methylquinoline are reacted, and the isolated crude product is reduced with 102 mg (2.70 mmol) of NaBH4. After chromatography on silica gel with hexane-ethyl acetate, 165 mg of product is obtained.

Workup

  1. customthe isolated crude product

Sources & evidence

ORD record
ord-ba75efb8185c45658b8432919dfb07e6
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

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