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Ammonia → 5-[6-(aminomethyl)-3H-imidazo[4,5-c]pyridin-3-yl]-3-{(1R)-1-[2-(trifluoromethyl)phenyl]ethoxy}thiophene-2-carboxamide

HRID 2391615
ノート
印刷プレビュー

反応式

HRID 2391615 の反応式
CS(O[CH2:6][C:7]1[N:12]=[CH:11][C:10]2[N:13]([C:16]3[S:17][C:18]([C:34](=[O:36])[NH2:35])=[C:19]([O:21][C@@H:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]([F:33])([F:32])[F:31])[CH3:23])[CH:20]=3)[CH:14]=[N:15][C:9]=2[CH:8]=1)(=O)=O.[NH3:37]>CO>[NH2:37][CH2:6][C:7]1[N:12]=[CH:11][C:10]2[N:13]([C:16]3[S:17][C:18]([C:34]([NH2:35])=[O:36])=[C:19]([O:21][C@@H:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]([F:33])([F:31])[F:32])[CH3:23])[CH:20]=3)[CH:14]=[N:15][C:9]=2[CH:8]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 222AmmoniaHCID 86647106[3-(5-carbamoyl-4-{(1R)-1-[2-(trifluoromethyl)phenyl]ethoxy}-2-thienyl)-3H-imidazo[4,5-c]pyridin-6-yl]methyl methanesulfonate

生成物 1

HCID 687669945-[6-(aminomethyl)-3H-imidazo[4,5-c]pyridin-3-yl]-3-{(1R)-1-[2-(trifluoromethyl)phenyl]ethoxy}thiophene-2-carboxamide

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
80 °C

実験手順

A suspension of 150 mg of crude [3-(5-carbamoyl-4-{(1R)-1-[2-(trifluoromethyl)phenyl]ethoxy}-2-thienyl)-3H-imidazo[4,5-c]pyridin-6-yl]methyl methanesulfonate (example 49, step 1) in 5 ml of a saturated solution of ammonia in methanol is stirred in a microwave vial at 80° C. for 1 h in the microwave cavity. The solvent is removed under reduced pressure. 20 ml of water and 20 ml dichloromethane is added to the residue, the organic phase is separated and the aqueous phase is extracted with 2×10 ml dichloromethane. The combined organic layers are dried over MgSO4, filtered and evaporated under reduced pressure. The resulting residue is purified by flash chromatography [silica gel, eluent: dichloromethane/methanol/7 N solution of ammonia in methanol, 9/1/0.3 (v/v/v)] to yield the title product.

後処理

  1. customThe solvent is removed under reduced pressure
  2. addition20 ml of water and 20 ml dichloromethane is added to the residue
  3. customthe organic phase is separated
  4. extractionthe aqueous phase is extracted with 2×10 ml dichloromethane
  5. dry with materialThe combined organic layers are dried over MgSO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe resulting residue is purified by flash chromatography [silica gel, eluent: dichloromethane/methanol/7 N solution of ammonia in methanol, 9/1/0.3 (v/v/v)]

出典と根拠

ORDレコード
ord-8c1d458b8d1648348a74b2705c079b7b
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08273890B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート