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

HRID 1428734Notes

Reaction equation

HRID 1428734 reaction equation
[C:1]1([CH3:19])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C:12]([CH2:13][NH2:14])=[CH:11][CH:10]=[C:9]([C:15]([F:18])([F:17])[F:16])[N:8]=2)[CH:2]=1.[F:20][C:21]1[CH:22]=[C:23]([CH:33]([CH3:37])[C:34](O)=[O:35])[CH:24]=[CH:25][C:26]=1[CH2:27][NH:28][S:29]([CH3:32])(=[O:31])=[O:30].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>[F:20][C:21]1[CH:22]=[C:23]([CH:33]([CH3:37])[C:34]([NH:14][CH2:13][C:12]2[C:7]([C:3]3[CH:2]=[C:1]([CH3:19])[CH:6]=[CH:5][CH:4]=3)=[N:8][C:9]([C:15]([F:16])([F:18])[F:17])=[CH:10][CH:11]=2)=[O:35])[CH:24]=[CH:25][C:26]=1[CH2:27][NH:28][S:29]([CH3:32])(=[O:31])=[O:30]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 866793652-(3-Fluoro-4-(methylsulfonamidomethyl)phenyl)propanoic acidHCID 86680208(2-m-Tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine

Product 1

HCID 715396882-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamideYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine (3.5 g, 13.143 mmol) and 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanoic acid (5.415 g, 19.715 mmol) in tetrahydrofuran (102 mL) was added 1-hydroxybenzotriazolhydrate (1.834 mL, 13.143 mmol), O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (4.213 g, 13.143 mmol) and N-ethyldiisopropylamine (6.676 mL, 39.429 mmol). The reaction mixture was stirred for 48 h. The reaction mixture was concentrated under reduced pressure and the solid obtained was purified by column chromatography (silica gel: 100-200 mesh, eluent: ethyl acetate/cyclohexane 2:1) to afford a white solid (2.65 mg, 32%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe solid obtained
  3. customwas purified by column chromatography (silica gel: 100-200 mesh, eluent: ethyl acetate/cyclohexane 2:1)

Sources & evidence

ORD record
ord-32b5b3c799cc45ff82f8d974c1f60e70
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

Loading…