HCID 18450643, compound → 3-(4-Amino-3-phenylthieno[3,2-c]pyridin-7-yl)-N-methylpropanamide

HRID 2390618Notes

Reaction equation

HRID 2390618 reaction equation
[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][S:10][C:6]=2[C:5](/[CH:17]=[CH:18]/[C:19]([NH:21][CH3:22])=[O:20])=[CH:4][N:3]=1>[Pd].CO.CN(C=O)C>[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][S:10][C:6]=2[C:5]([CH2:17][CH2:18][C:19]([NH:21][CH3:22])=[O:20])=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 18450643HCID 18450643, compound

Product 1

HCID 184507113-(4-Amino-3-phenylthieno[3,2-c]pyridin-7-yl)-N-methylpropanamideYield 83.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21901440N,N-dimethylformamide methanolSolvent

Procedure

A mixture of Example 14 (30 mg, 0.1 mmol) and 10% Pd on carbon (30 mg) in 1:1 methanol/DMF (4 mL) was stirred under an atmosphere of hydrogen overnight. The suspension was filtered through diatomaceous earth (Celite®). The pad was washed with methanol and the filtrate was concentrated to half its original volume. The residue was diluted with diethyl ether and filtered. The filter cake was dried to provide 26 mg of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 2.47 (m, 2H), 2.58 (d, J=4.6 Hz, 2H), 2.91 (t, J=7.9 Hz, 2H), 5.21 (s, 1H), 7.50 (m, 6H), 7.66 (s, 1H), 7.81 (m, J=4.3 Hz, 1H); MS (ESI(+)) m/e 312 (M+H)+.

Workup

  1. filtrationThe suspension was filtered through diatomaceous earth (Celite®)
  2. washThe pad was washed with methanol
  3. concentrationthe filtrate was concentrated to half its original volume
  4. additionThe residue was diluted with diethyl ether
  5. filtrationfiltered
  6. customThe filter cake was dried

Sources & evidence

ORD record
ord-abfc0510bb6443b28cef74af66b5bf0e
Source dataset
uspto-grants-2012_09
Patent number
US08273736B2

Reaction notes

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