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1-Hydroxybenzotriazole → 2-[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-[3-(trifluoro-methyl)phenylmethyl]-acetamide

HRID 660917
Notes
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Reaction equation

HRID 660917 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:15][CH2:14]3)[C:11](=[O:16])[N:10]([CH2:17][C:18]([OH:20])=O)[N:9]=2)=[CH:4][CH:3]=1.[F:21][C:22]([F:32])([F:31])[C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26][NH2:27].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH:13]3[CH2:14][CH2:15]3)[C:11](=[O:16])[N:10]([CH2:17][C:18]([NH:27][CH2:26][C:25]3[CH:28]=[CH:29][CH:30]=[C:23]([C:22]([F:21])([F:31])[F:32])[CH:24]=3)=[O:20])[N:9]=2)=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 759623-(Trifluoromethyl)benzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 42632357[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetic acid

Product 1

HCID 24864192
2-[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-[3-(trifluoro-methyl)phenylmethyl]-acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50.0 mg (0.170 mmol) of [3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetic acid from Example 88A and 32.8 mg (0.187 mmol) of 3-trifluoromethylbenzylamine are placed in 2 ml dimethylformamide and treated with 27.6 mg (0.204 mmol) of HOBt. After 10 mins' stirring, 42.4 mg (0.221 mmol) of EDC hydrochloride are added and the mixture stirred overnight at room temperature. For the workup, the reaction mixture is partitioned between dichloromethane and water, and the organic phase is separated, dried over sodium sulphate and concentrated. The residue is purified by flash chromatography on silica gel (eluent: dichloromethane/methanol first 200:1, then 100:1) and thus yields 76 mg (99% of theory) of the target compound.

Workup

  1. stirringthe mixture stirred overnight at room temperature
  2. customFor the workup, the reaction mixture is partitioned between dichloromethane and water
  3. customthe organic phase is separated
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customThe residue is purified by flash chromatography on silica gel (eluent

Sources & evidence

ORD record
ord-4b977c1381ec45578a0033b900464c15
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08084481B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes