3-(4-Aminophenyl)-7-[4-(benzyloxy)phenyl]thieno[3,2-c]pyridin-4-amine → HCID 18450816, compound

HRID 2390630Notes

Reaction equation

HRID 2390630 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[C:13]([NH2:31])=[N:14][CH:15]=[C:16]([C:17]4[CH:22]=[CH:21][C:20]([O:23]CC5C=CC=CC=5)=[CH:19][CH:18]=4)[C:11]=3[S:10][CH:9]=2)=[CH:4][CH:3]=1>Br.C(O)(=O)C>[NH2:31][C:13]1[C:12]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH2:1])=[CH:7][CH:6]=3)=[CH:9][S:10][C:11]=2[C:16]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)=[CH:15][N:14]=1

Participants

4

Reactant 1

HCID 184507393-(4-Aminophenyl)-7-[4-(benzyloxy)phenyl]thieno[3,2-c]pyridin-4-amine

Product 1

HCID 18450816HCID 18450816, compoundYield 125.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

A suspension of Example 138 (132 mg) in 48% HBr (2 mL) and acetic acid (4 mL) was heated to 80° C. for 3 hours. The resulting homogeneous solution was concentrated and the residue was triturated from ethanol/diethyl ether to provide 130 mg of the desired product the dihydrobromide salt. 1H NMR (300 MHz, DMSO-d6) δ 3.67 (s, 2H), 6.95-6.98 (m, 6H), 7.34 (d, J=8.48 Hz, 2H), 7.51 (d, J=8.82 Hz, 2H), 7.85 (d, J=8.82 Hz, 2H), 9.83 (s, 1H); MS (ESI(+)) m/e 334 (M+H)+.

Workup

  1. concentrationThe resulting homogeneous solution was concentrated
  2. customthe residue was triturated from ethanol/diethyl ether

Sources & evidence

ORD record
ord-c27dca844f674281a226060c0802b20d
Source dataset
uspto-grants-2012_09
Patent number
US08273736B2

Reaction notes

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