Diisopropylethylamine → (+/-)-3-({6-[1-(3-Trifluoromethyl-phenylcarbamoyl)-1H-indol-5-yloxy]-pyrimidin-4-ylmethyl}-amino)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 453184

反応式

HRID 453184 の反応式
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([O:21][C:22]4[N:27]=[CH:26][N:25]=[C:24]([CH2:28]OS(C)(=O)=O)[CH:23]=4)=[CH:18][CH:19]=3)[CH:14]=[CH:13]2)=[O:11])[CH:6]=[CH:7][CH:8]=1.[C:36]([O:40][C:41]([N:43]1[CH2:47][CH2:46][CH:45]([NH2:48])[CH2:44]1)=[O:42])([CH3:39])([CH3:38])[CH3:37].C(N(C(C)C)CC)(C)C>C1COCC1.CCOC(C)=O>[C:36]([O:40][C:41]([N:43]1[CH2:47][CH2:46][CH:45]([NH:48][CH2:28][C:24]2[CH:23]=[C:22]([O:21][C:17]3[CH:16]=[C:15]4[C:20](=[CH:19][CH:18]=3)[N:12]([C:10](=[O:11])[NH:9][C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:35])([F:34])[F:1])[CH:4]=3)[CH:13]=[CH:14]4)[N:27]=[CH:26][N:25]=2)[CH2:44]1)=[O:42])([CH3:39])([CH3:37])[CH3:38]

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 27563701-Boc-3-aminopyrrolidineHCID 46224264methanesulfonic acid 6-[1-(3-trifluoromethyl-phenylcarbamoyl)-1H-indol-5-yloxy]-pyrimidin-4-ylmethyl ester

生成物 1

HCID 59394560(+/-)-3-({6-[1-(3-Trifluoromethyl-phenylcarbamoyl)-1H-indol-5-yloxy]-pyrimidin-4-ylmethyl}-amino)-pyrrolidine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

To the solution of methanesulfonic acid (±)-6-[1-(3-trifluoromethyl-phenylcarbamoyl)-1H-indol-5-yloxy]-pyrimidin-4-ylmethyl ester (80 mg, 0.158 mmol) in THF (5 mL), 3-amino-pyrrolidine-1-carboxylic acid tert-butyl ester (88 mg, 0.474 mmol) and diisopropylethylamine (61 mg, 0.474 mmol) are added. The resulting solution is stirred at 60° C. overnight. After cooling to rt, the reaction mixture is diluted with EtOAc and washed with water and then brine. The organic layer is dried with anhydrous Na2SO4, filtered, and condensed. The residue is purified by FCC (0-10% MeOH/DCM) to provide the title compound. MS (ESI) m/z 597.2 (M+1).

後処理

  1. temperatureAfter cooling to rt
  2. washwashed with water
  3. dry with materialThe organic layer is dried with anhydrous Na2SO4
  4. filtrationfiltered
  5. customcondensed
  6. customThe residue is purified by FCC (0-10% MeOH/DCM)

出典と根拠

ORDレコード
ord-451bfadfbedb4d56a477c5133ae61714
出典データセット
uspto-grants-2013_07
特許番号
US08492393B2

関連ノート

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