Hydrochloric Acid → HCID 16659816, compound

HRID 1362307Notes

Reaction equation

HRID 1362307 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([N:12]([CH2:14][C:15]2[S:19][C:18]3[C:20]([F:24])=[CH:21][CH:22]=[CH:23][C:17]=3[C:16]=2[Cl:25])[CH3:13])=[O:11])=[CH:4][CH:3]=1.Cl>C(Cl)Cl.CCOCC>[ClH:25].[NH2:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([N:12]([CH2:14][C:15]2[S:19][C:18]3[C:20]([F:24])=[CH:21][CH:22]=[CH:23][C:17]=3[C:16]=2[Cl:25])[CH3:13])=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 16659817HCID 16659817, compound

Product 1

HCID 16659816HCID 16659816, compoundYield 192.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A suspension of (E)-3-(6-amino-pyridin-3-yl)-N-(3-chloro-7-fluoro-benzo[b]thiophen-2-ylmethyl)-N-methylacrylamide (105 mg, 0.28 mmol) in CH2Cl2 (10 mL) was treated with anhydrous HCl (0.28 mL of a 1.0 M solution in Et2O, 0.28 mmol) and then the mixture was stirred at room temperature overnight. The mixture was diluted with Et2O. The resulting solid was collected by filtration and dried under vacuum at 50° C. overnight to give the title compound (111 mg, 96%) as an off-white solid and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 8.43-8.33 (m, 4H), 7.67-7.52 (m, 3H), 7.41-7.35 (m, 1H), 7.25-7.19 (m, 1H), 7.04-7.01 (m, 1H), 5.21-4.92 (m, 2H), 3.63 (br s, 1H), 3.23-2.98 (m, 3H); MS (ESI) m/e 376 (M+H)+.

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. customdried under vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-7d3a50ebd7b84fecb168cd4ae1fe027e
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

Loading…