Triethylamine → 3,4-dimethoxyphenyl 2-[(2-aminophenyl)carbamoyl]-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate

HRID 2093093ノート

反応式

HRID 2093093 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[S:19][C:18]2[CH2:17][CH2:16][NH:15][CH2:14][C:13]=2[CH:12]=1)=[O:10].[N+](C1C=CC([O:29][C:30](=O)[O:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[C:34]([O:40][CH3:41])[CH:33]=2)=CC=1)([O-])=O.CCN(CC)CC>CN(C=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[S:19][C:18]2[CH2:17][CH2:16][N:15]([C:30]([O:31][C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[C:34]([O:40][CH3:41])[CH:33]=3)=[O:29])[CH2:14][C:13]=2[CH:12]=1)=[O:10]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 44203072Carbonic acid 3,4-dimethoxy-phenyl ester 4-nitro-phenyl esterHCID 58117019N-(2-aminophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxamide

生成物 1

HCID 252301123,4-dimethoxyphenyl 2-[(2-aminophenyl)carbamoyl]-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

To a solution of N-(2-aminophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxamide (1.0 eq) obtained in step VIII of example 203 in DMF was treated with Carbonic acid 3,4-dimethoxy-phenyl ester 4-nitro-phenyl ester (1.0 eq) in presence of base like Et3N and stirred at 50° C. for 8 h Reaction was then quenched with water and extracted with ethyl acetate and the organic layer was separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude product, which, on purification by column chromatography afforded the title compound.

後処理

  1. customReaction
  2. customwas then quenched with water
  3. extractionextracted with ethyl acetate
  4. customthe organic layer was separated
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto afford crude product, which
  8. customon purification by column chromatography

出典と根拠

ORDレコード
ord-f386ded5e28b4d31962997c065e16f6a
出典データセット
uspto-grants-2013_05
特許番号
US08440830B2

反応ノート

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