Diisopropylethylamine → HCID 71610613、化合物

HRID 1481842ノート

反応式

HRID 1481842 の反応式
[CH:1]1([C:4]2[O:5][CH:6]=[C:7]([C:9]([OH:11])=O)[N:8]=2)[CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.[NH2:21][C:22]1[C:23]([N:41]2[CH2:46][CH2:45][N:44]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=3[CH3:53])[CH2:43][CH2:42]2)=[CH:24][C:25]([Cl:40])=[C:26]([CH:39]=1)[C:27]([NH:29][CH2:30][CH2:31][CH2:32][N:33]1[CH2:37][CH2:36][CH2:35][C:34]1=[O:38])=[O:28].[Cl-].[Li+]>CN(C=O)C>[Cl:40][C:25]1[C:26]([C:27](=[O:28])[NH:29][CH2:30][CH2:31][CH2:32][N:33]2[CH2:37][CH2:36][CH2:35][C:34]2=[O:38])=[CH:39][C:22]([NH:21][C:9]([C:7]2[N:8]=[C:4]([CH:1]3[CH2:2][CH2:3]3)[O:5][CH:6]=2)=[O:11])=[C:23]([N:41]2[CH2:42][CH2:43][N:44]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=3[CH3:53])[CH2:45][CH2:46]2)[CH:24]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 433294Lithium ChlorideHCID 252192732-Cyclopropyl-1,3-oxazole-4-carboxylic acidHCID 89690513HCID 89690513、化合物

生成物 1

HCID 71610613HCID 71610613、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of 2-cyclopropyl-oxazole-4-carboxylic acid 1h (122.2 mg, 0.79 mmol) in DMF (5.0 mL) HATU (404.4 mg, 1.06 mmol) was added and stirred for 3 min. N,N-diisopropylethylamine (0.46 mL, 2.66 mmol) was added to this followed by 5-amino-2-chloro-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-4-(4-o-tolyl-piperazin-1-yl)-benzamide 1g (250.0 mg, 0.53 mmol) in DMF (5.0 mL) and the reaction was stirred at 25° C. for 16 h. LCMS indicated the completion of reaction. Saturated solution of lithium chloride was added to this and the contents were extracted with ethyl acetate, organic layer was dried on anhydrous sodium sulfate, concentrated and the crude ii was purified on preparative HPLC using water/methanol (0.1% TFA) (42.0 mg, 13%).

後処理

  1. stirringthe reaction was stirred at 25° C. for 16 h
  2. customthe completion of reaction
  3. extractionwere extracted with ethyl acetate, organic layer
  4. dry with materialwas dried on anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customthe crude ii was purified on preparative HPLC

出典と根拠

ORDレコード
ord-c04eac8984134dd491a5566c15ff823e
出典データセット
uspto-grants-2016_08
特許番号
US09409897B2

反応ノート

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