[(S)-1-Methyl-2-(7-{[(pyridine-3-carbonyl)-amino]-methyl}-furo[2,3-g]indazol-1-yl)-ethyl]-carbamic acid benzyl ester → N-[1-((S)-2-Aminopropyl)-1H-furo[2,3-g]indazol-7-ylmethyl]-nicotinamide

HRID 1453902Notes

Reaction equation

HRID 1453902 reaction equation
C(OC(=O)[NH:10][C@@H:11]([CH3:35])[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]3[O:24][C:23]([CH2:25][NH:26][C:27]([C:29]4[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=4)=[O:28])=[CH:22][C:20]3=2)[CH:15]=[N:14]1)C1C=CC=CC=1>CO.[Pd]>[NH2:10][C@@H:11]([CH3:35])[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]3[O:24][C:23]([CH2:25][NH:26][C:27](=[O:28])[C:29]4[CH:34]=[CH:33][CH:32]=[N:31][CH:30]=4)=[CH:22][C:20]3=2)[CH:15]=[N:14]1

Participants

4

Reactant 1

HCID 68857650[(S)-1-Methyl-2-(7-{[(pyridine-3-carbonyl)-amino]-methyl}-furo[2,3-g]indazol-1-yl)-ethyl]-carbamic acid benzyl ester

Product 1

HCID 68856074N-[1-((S)-2-Aminopropyl)-1H-furo[2,3-g]indazol-7-ylmethyl]-nicotinamideYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of the product from Step C (0.16 g, 0.33 mmol) in methanol (20 mL) was added 10% Palladium on carbon (20 mg) and this mixture was stirred under an atmosphere of hydrogen at room temperature for two days. The reaction mixture was filtered and the filtrate evaporated to give a colorless oil (0.10 g, 87%): LC/MS m/z 350 [M+H]+; 1H NMR (CD3OD) δ 9.052 (s, 1H), 8.70 (m, 1H), 8.31 (m, 1H), 8.08 (s, 1H), 7.62 and 7.36 (ABq, J=9 Hz, 2H), 7.56 (m, 1H), 4.50 (overlapping m and s, 4H), 3.47 (m, 1H), 1.08 (d, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-03855397ac06412193c0f90371ca12c1
Source dataset
uspto-grants-2009_01
Patent number
US07476687B2

Reaction notes

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