Benzyl 3-(1-carbamoyl-6-morpholino-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylcarbamate → 4-(3-Amino-2-methylphenyl)-6-morpholino-9H-pyrido[3,4-b]indole-1-carboxamide

HRID 2361348ノート

反応式

HRID 2361348 の反応式
[C:1]([C:4]1[C:9]2[NH:10][C:11]3[C:16]([C:8]=2[C:7]([C:23]2[C:24]([CH3:40])=[C:25]([NH:29]C(=O)OCC4C=CC=CC=4)[CH:26]=[CH:27][CH:28]=2)=[CH:6][N:5]=1)=[CH:15][C:14]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[CH:13][CH:12]=3)(=[O:3])[NH2:2]>CO.C1COCC1.[Pd]>[NH2:29][C:25]1[C:24]([CH3:40])=[C:23]([C:7]2[C:8]3[C:16]4[C:11](=[CH:12][CH:13]=[C:14]([N:17]5[CH2:18][CH2:19][O:20][CH2:21][CH2:22]5)[CH:15]=4)[NH:10][C:9]=3[C:4]([C:1]([NH2:2])=[O:3])=[N:5][CH:6]=2)[CH:28]=[CH:27][CH:26]=1

参加物

5

反応物 1

HCID 67994849Benzyl 3-(1-carbamoyl-6-morpholino-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylcarbamate

生成物 1

HCID 679946124-(3-Amino-2-methylphenyl)-6-morpholino-9H-pyrido[3,4-b]indole-1-carboxamide収率 84.1%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of benzyl 3-(1-carbamoyl-6-morpholino-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylcarbamate (0.125 g, 0.233 mmol) and 10% Pd/C (0.025 g, 0.023 mmol) in methanol (8.75 mL) and THF (2.92 mL) was stirred under a hydrogen balloon. After 1 hr, the reaction was flushed with nitrogen, filtered through a pad of CELITE®, rinsed with MeOH. The filtrate was concentrated in vacuo, dissolved in CH2Cl2 (100 mL), dried over MgSO4, and concentrated in vacuo to give the desired product (0.0786 g, 0.196 mmol, 84% yield) as a light tan solid.

後処理

  1. customthe reaction was flushed with nitrogen
  2. filtrationfiltered through a pad of CELITE®
  3. washrinsed with MeOH
  4. concentrationThe filtrate was concentrated in vacuo
  5. dissolutiondissolved in CH2Cl2 (100 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-eefaa0b7a75c43ec8bdfd419636387f0
出典データセット
uspto-grants-2014_04
特許番号
US08685969B2

反応ノート

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