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benzyl 1-carbamoyl-4-(2-fluorophenyl)-9H-pyrido[3,4-b]indol-7-ylcarbamate → 7-amino-4-(2-fluorophenyl)-9H-pyrido[3,4-b]indole-1-carboxamide

HRID 2361262
ノート
印刷プレビュー

反応式

HRID 2361262 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:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[F:34])=[CH:6][N:5]=1)=[CH:15][CH:14]=[C:13]([NH:17]C(=O)OCC1C=CC=CC=1)[CH:12]=3)(=[O:3])[NH2:2]>O1CCCC1.CO.[Pd]>[NH2:17][C:13]1[CH:12]=[C:11]2[C:16]([C:8]3[C:7]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[F:34])=[CH:6][N:5]=[C:4]([C:1]([NH2:2])=[O:3])[C:9]=3[NH:10]2)=[CH:15][CH:14]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 1

HCID 70651623benzyl 1-carbamoyl-4-(2-fluorophenyl)-9H-pyrido[3,4-b]indol-7-ylcarbamate

生成物 1

HCID 679945367-amino-4-(2-fluorophenyl)-9H-pyrido[3,4-b]indole-1-carboxamide収率 90.1%

試薬・触媒・溶媒 3

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

実験手順

A mixture of benzyl 1-carbamoyl-4-(2-fluorophenyl)-9H-pyrido[3,4-b]indol-7-ylcarbamate (210 mg, 0.416 mmol) and 10% Pd/C (45 mg, 0.042 mmol) in tetrahydrofuran (5 mL) and methanol (15 mL) was stirred under H2, provided with a H2 balloon, at rt for 1 hr. The catalyst was removed by suction filtration through CELITE®. The filtrate was concentrated under vacuum. The residue was diluted with CH2Cl2 (100 mL), washed with brine (30 mL), and dried over anhydrous MgSO4. Removal of solvent under vacuum provided the desired product, 7-amino-4-(2-fluorophenyl)-9H-pyrido[3,4-b]indole-1-carboxamide (132 mg, 0.375 mmol, 90% yield), as a tan solid. LCMS (M+H)+=321.10.

後処理

  1. customprovided with a H2 balloon, at rt for 1 hr
  2. customThe catalyst was removed by suction filtration through CELITE®
  3. concentrationThe filtrate was concentrated under vacuum
  4. additionThe residue was diluted with CH2Cl2 (100 mL)
  5. washwashed with brine (30 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. customRemoval of solvent under vacuum

出典と根拠

ORDレコード
ord-40a08ec7aa9d464eae031d9ae6e3b845
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08685969B2

反応ノート

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