Tert-butyl 4-[4-amino-7-(4-pyridinyl)thieno[3,2-c]pyridin-3-yl]phenylcarbamate → 3-(4-Aminophenyl)-7-(pyridin-4-yl)thieno[3,2-c]pyridin-4-amine

HRID 2390628Notes

Reaction equation

HRID 2390628 reaction equation
[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17]C(=O)OC(C)(C)C)=[CH:13][CH:12]=3)=[CH:9][S:10][C:6]=2[C:5]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)=[CH:4][N:3]=1>ClCCl>[NH2:17][C:14]1[CH:13]=[CH:12][C:11]([C:8]2[C:7]3[C:2]([NH2:1])=[N:3][CH:4]=[C:5]([C:25]4[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=4)[C:6]=3[S:10][CH:9]=2)=[CH:16][CH:15]=1

Participants

3

Reactant 1

HCID 18451458Tert-butyl 4-[4-amino-7-(4-pyridinyl)thieno[3,2-c]pyridin-3-yl]phenylcarbamate

Product 1

HCID 184507433-(4-Aminophenyl)-7-(pyridin-4-yl)thieno[3,2-c]pyridin-4-amineYield 129%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 121A (0.11 g, 0.263 mmol) in TEA (3 mL) and dichloromethane (1 mL) was stirred at room temperature for 30 minutes and concentrated under a stream of nitrogen. The residue was triturated from ethyl acetate/hexanes to provide 108 mg of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 5.66 (s, 2H), 6.78 (d, J=8.14 Hz, 2H), 6.97 (s, 2H), 7.20 (d, J=8.48 Hz, 2H), 7.75 (s, 1H), 7.91 (d, J=6.44 Hz, 2H), 8.19 (s, 1H), 8.83 (d, J=6.44 Hz, 2H); MS (ESI(+)) m/e 319 (M+H)+.

Workup

  1. concentrationconcentrated under a stream of nitrogen
  2. customThe residue was triturated from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-898451412dcb4d1786532f7015a4e61e
Source dataset
uspto-grants-2012_09
Patent number
US08273736B2

Reaction notes

Loading…