2-Chloro-3-(trifluoromethyl)benzoic acid → (+/-)-2-Chloro-N-[[1-(methylamino)cyclopentyl](phenyl)methyl]-3-(trifluoromethyl)benzamide

HRID 20842

반응식

HRID 20842 반응식
[Cl:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:15][CH:16]([C:23]1(CN)[CH2:27][CH2:26][CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH3:30][N:31](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCN(C(C)C)C(C)C>[Cl:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:15][CH:16]([C:23]1([NH:31][CH3:30])[CH2:24][CH2:25][CH2:26][CH2:27]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:6]

참가 물질

6

반응물 3

HCID 27366772-Chloro-3-(trifluoromethyl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57444874{[Amino(phenyl)methyl]cyclopentyl}methylamine

생성물 1

HCID 59347824(+/-)-2-Chloro-N-[[1-(methylamino)cyclopentyl](phenyl)methyl]-3-(trifluoromethyl)benzamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 81531Diisopropylethylamine용매

실험 절차

To a solution of 2-chloro-3-(trifluoromethyl)benzoic acid (0.728 g; 3.24 mmol) in DMF (20 ml) and DIPEA (2.5 ml) was added (±)-{[amino(phenyl)methyl]cyclopentyl}methylamine D29 (1.0 g; 3.60 mmol) and HATU (1.23 g; 3.24 mmol). The resulting mixture was allowed to stir at room temperature overnight and then DMF evaporated off in vacuo. Residual material was partitioned between ethyl acetate and water. The organic layer was dried (Na2SO4) and the filtrate evaporated in vacuo. The desired product was isolated by column chromatography on silica gel using 20% diethyl ether to 100% diethyl ether in n-pentane to afford the title compound as a white solid (0.908 g; 61%). 1H NMR (CDCl3) δ: 1.47-1.83 (9H, m), 2.21 (3H, s), 5.1 (1H, m), 7.23-7.43 (6H, m), 7.58 (1H, m), 7.65 (1H, m), 7.73 (1H, m); Mass Spectrum (Electrospray LC/MS), API+: Found 411 (MH+). C21H2235ClF3N2O requires 410. Ret. time 2.04 min.

후처리

  1. customDMF evaporated off in vacuo
  2. customResidual material was partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customthe filtrate evaporated in vacuo

출처 및 근거

ORD 기록
ord-52e008b438bc49e8b5555b7bdf07b14c
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745642B2

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