Triethylamine → HCID 11202011、化合物

HRID 1173006

反応式

HRID 1173006 の反応式
[CH:1]([C:4]1[N:5]=[C:6]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[S:7][C:8]=1[CH2:9]O)([CH3:3])[CH3:2].CCN(CC)CC.CS(Cl)(=O)=O.[NH2:33][C:34]1[CH:39]=[CH:38][C:37]([C@@H:40]2[CH2:42][C@H:41]2[C:43]([OH:45])=[O:44])=[CH:36][CH:35]=1>ClCCl.O>[CH:1]([C:4]1[N:5]=[C:6]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[S:7][C:8]=1[CH2:9][NH:33][C:34]1[CH:35]=[CH:36][C:37]([C@@H:40]2[CH2:42][C@H:41]2[C:43]([OH:45])=[O:44])=[CH:38][CH:39]=1)([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 587657624-Isopropyl-2-[4-(trifluoromethyl)phenyl]thiazole-5-methanolHCID 68668314(1R,2R)-2-(4-aminophenyl)cyclopropane-1-carboxylic acid

生成物 1

HCID 11202011HCID 11202011、化合物収率 19.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of {(4-isopropyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methanol (0.10 g, 0.331 mmol) in dichloromethane (3 mL) was added Et3N (0.04 g, 0.39 mmol) and the mixture cooled to 0° C. The mixture stirred for 15 min after which methanesulfonyl chloride (0.04 g, 0.36 mmol) was added followed 30 min later by the addition of racemic-(trans)-2-(4-aminophenyl)cyclopropanecarboxylic acid (I-1) (0.09 g, 0.49 mmol). The solution stirred for 24 h after which it was poured into H2O, the organics extracted with dichloromethane, dried over MgSO4, and the solvents reduced in vacuo. The crude material was purified on silica gel eluting with an increasing gradient from hexanes to 30% ethyl acetate/hexanes to give the title compound as a yellow powder (0.03 g, 16%). 1H NMR (400 MHz, CDCl3) δ 8.01 (d, J=8.3 Hz, 2H), 7.65 (d, J=8.2 Hz, 2H), 6.98 (d, J=8.4 Hz, 2H), 6.62 (d, J=8.6 Hz, 2H), 4.47 (s, 2H), 3.50-3.47 (m, 1H), 3.18-3.15 (m, 1H), 2.53-2.51 (m, 1H), 1.80-1.77 (m, 1H), 1.61-1.58 (m, 1H), 1.37-1.26 (m, 7H).

後処理

  1. additionwas added
  2. extractionthe organics extracted with dichloromethane
  3. dry with materialdried over MgSO4
  4. customThe crude material was purified on silica gel eluting with an increasing gradient from hexanes to 30% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-ee78b6a53a9e4997a25bbcdb804911dd
出典データセット
uspto-grants-2010_11
特許番号
US07834013B2

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