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

HRID 20842

反応式

HRID 20842 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 81531Diisopropylethylamine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-52e008b438bc49e8b5555b7bdf07b14c
出典データセット
uspto-grants-2010_06
特許番号
US07745642B2

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