Isopropylamine → Racemic-(trans)-n-isopropyl-2-{4-[({4-isopropyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)amino]phenyl}cyclopropanecarboxamide

HRID 1173033

反応式

HRID 1173033 の反応式
[CH:1]([C:4]1[N:5]=[C:6]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)[S:7][C:8]=1[CH2:9][NH:10][C:11]1[CH:16]=[CH:15][C:14]([C@@H:17]2[CH2:19][C@H:18]2[C:20](O)=[O:21])=[CH:13][CH:12]=1)([CH3:3])[CH3:2].CN(C(ON1N=[N:48][C:43]2[CH:44]=CC=N[C:42]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N)(C)C>ClCCl.CN(C=O)C>[CH:43]([NH:48][C:20]([C@@H:18]1[CH2:19][C@H:17]1[C:14]1[CH:15]=[CH:16][C:11]([NH:10][CH2:9][C:8]2[S:7][C:6]([C:23]3[CH:24]=[CH:25][C:26]([C:29]([F:32])([F:30])[F:31])=[CH:27][CH:28]=3)=[N:5][C:4]=2[CH:1]([CH3:2])[CH3:3])=[CH:12][CH:13]=1)=[O:21])([CH3:44])[CH3:42]

参加物

6

反応物 3

HCID 6363IsopropylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11202011Racemic-(trans)-2-{4-[({4-isopropyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)amino]phenyl}cyclopropanecarboxylic acid

生成物 1

HCID 11752407Racemic-(trans)-n-isopropyl-2-{4-[({4-isopropyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)amino]phenyl}cyclopropanecarboxamide収率 22%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a mixture of racemic-(trans)-2-{4-[({4-isopropyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)amino]phenyl}cyclopropanecarboxylic acid (I-2n) (0.05 g, 0.11 mmol) in dichloromethane (3 mL) and DMF (1 mL) was added HATU (0.06 g, 0.16 mmol). The mixture was stirred for 15 min followed by addition of isopropylamine (0.01 g, 0.16 mmol). The solution stirred for 3 h after which the dichloromethane was removed via rotavap. Sat. NaHCO3 and ethyl acetate were added and the organic layer separated and washed with H2O, dried over MgSO4, filtered and concentrated. The resulting oil was triterated with Et2O and formed a white ppt which was filtered and dried under high vacuum to give the title compound as a white powder (0.01 g, 22%). 1H NMR (400 MHz, CDCl3) δ 7.99 (d, 8.3 Hz, 2H), 7.63 (d, J=8.2 Hz, 2H), 6.94 (d, J=8.4 Hz, 2H), 6.60 (d, J=8.5 Hz, 2H), 5.37 (d, J=7.9 Hz, 1H), 4.45 (s, 2H), 4.10-4.08 (m, 1H), 3.93 (s, 1H), 3.16-3.13 (m, 1H), 2.39-2.37 (m, 1H), 1.54-1.50 (m, 1H), 1.42-1.39 (m, 1H), 1.35 (d, J=6.8 Hz, 6H), 1.15-1.09 (m, 7H).

後処理

  1. customwas removed via rotavap
  2. additionSat. NaHCO3 and ethyl acetate were added
  3. customthe organic layer separated
  4. washwashed with H2O
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customformed a white ppt which
  9. filtrationwas filtered
  10. customdried under high vacuum

出典と根拠

ORDレコード
ord-917d3439307743aa93ea060685d8d52b
出典データセット
uspto-grants-2010_11
特許番号
US07834013B2

関連ノート

読み込み中…