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 2361262Notes

Reaction equation

HRID 2361262 reaction equation
[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

Participants

5

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-40a08ec7aa9d464eae031d9ae6e3b845
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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