Diisopropylethylamine → N-((2-(3-chloro-4-fluorophenyl)-6-(trifluoromethyl)pyridin-3-yl)methyl)-2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanamide

HRID 1428721Notes

Reaction equation

HRID 1428721 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C:10]2[C:15]([CH2:16][NH2:17])=[CH:14][CH:13]=[C:12]([C:18]([F:21])([F:20])[F:19])[N:11]=2)[CH:6]=[CH:7][C:8]=1[F:9].[F:22][C:23]1[CH:24]=[C:25]([CH:35]([CH3:39])[C:36](O)=[O:37])[CH:26]=[CH:27][C:28]=1[CH2:29][NH:30][S:31]([CH3:34])(=[O:33])=[O:32].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C>O1CCCC1>[Cl:2][C:3]1[CH:4]=[C:5]([C:10]2[C:15]([CH2:16][NH:17][C:36](=[O:37])[CH:35]([C:25]3[CH:26]=[CH:27][C:28]([CH2:29][NH:30][S:31]([CH3:34])(=[O:32])=[O:33])=[C:23]([F:22])[CH:24]=3)[CH3:39])=[CH:14][CH:13]=[C:12]([C:18]([F:20])([F:21])[F:19])[N:11]=2)[CH:6]=[CH:7][C:8]=1[F:9]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86676125(2-(3-Chloro-4-fluorophenyl)-6-(trifluoromethyl)pyridin-3-yl)methanamine hydrochlorideHCID 866793652-(3-Fluoro-4-(methylsulfonamidomethyl)phenyl)propanoic acid

Product 1

HCID 71539579N-((2-(3-chloro-4-fluorophenyl)-6-(trifluoromethyl)pyridin-3-yl)methyl)-2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (2-(3-chloro-4-fluorophenyl)-6-(trifluoromethyl)pyridin-3-yl)methanamine hydrochloride (1.104 g, 3.632 mmol) and 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanoic acid (1 g, 3.632 mmol) in tetrahydrofuran (28 mL) was added 1-hydroxybenzotriazolhydrate (0.49 mL, 3.632 mmol), O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (1.166 g, 3.632 mmol) and N-ethyldiisopropylamine (1.852 mL, 10.896 mmol) and the reaction mixture was allowed to stir for 48 h. The reaction mixture was concentrated under reduced pressure and the solid obtained was purified by column chromatography (eluent:ethyl acetate/cyclohexane 2:1) to afford a white solid (example 16) (605 mg, 30%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe solid obtained
  3. customwas purified by column chromatography (eluent:ethyl acetate/cyclohexane 2:1)
  4. customto afford a white solid (example 16) (605 mg, 30%)

Sources & evidence

ORD record
ord-809254c0d9794e1295949c7cd60ca446
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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