Hydroxyamine hydrochloride → (2S)-1,1,1-trifluoro-2-[1-[[4-(4-fluorophenyl)-2-[(Z)-N-hydroxy-C-methylcarbonimidoyl]quinolin-7-yl]methyl]triazol-4-yl]butan-2-ol

HRID 2422565Notes

Reaction equation

HRID 2422565 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([CH2:18][N:19]4[CH:23]=[C:22]([C@:24]([OH:31])([C:27]([F:30])([F:29])[F:28])[CH2:25][CH3:26])[N:21]=[N:20]4)=[CH:15][CH:16]=3)[N:11]=[C:10]([C:32](=O)[CH3:33])[CH:9]=2)=[CH:4][CH:3]=1.Cl.[NH2:36][OH:37]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([CH2:18][N:19]4[CH:23]=[C:22]([C@:24]([OH:31])([C:27]([F:28])([F:30])[F:29])[CH2:25][CH3:26])[N:21]=[N:20]4)=[CH:15][CH:16]=3)[N:11]=[C:10](/[C:32](=[N:36]\[OH:37])/[CH3:33])[CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 66790923(S)-1-[4-(4-fluorophenyl)-7-({4-[1-hydroxy-1-(trifluoromethyl)propyl]-1H-1,2,3-triazol-1-yl}methyl)quinolin-2-yl]ethanone

Product 1

HCID 136381258(2S)-1,1,1-trifluoro-2-[1-[[4-(4-fluorophenyl)-2-[(Z)-N-hydroxy-C-methylcarbonimidoyl]quinolin-7-yl]methyl]triazol-4-yl]butan-2-ol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (S)-1-[4-(4-fluorophenyl)-7-({4-[1-hydroxy-1-(trifluoromethyl)propyl]-1H-1,2,3-triazol-1-yl}methyl)quinolin-2-yl]ethanone (50 mg, 0.11 mmol) and hydroxylamine hydrochloride (11 mg, 0.16 mmol) in pyridine (1 mL) was stirred at rt overnight. The solution was concentrated and purification on silica gel (eluting with acetone/dichloromethane, 2:8) gave the title compound. MS (+ESI): 488 (M+H)+.

Workup

  1. concentrationThe solution was concentrated
  2. custompurification on silica gel (eluting with acetone/dichloromethane, 2:8)

Sources & evidence

ORD record
ord-6d8fb97d4bce4f9c84501aaac5313ca5
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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