Hydrochloric Acid → HCID 16659814, compound

HRID 1362303Notes

Reaction equation

HRID 1362303 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[CH:20]=[CH:21][CH:22]=[C:23]([F:24])[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[CH:20]=[CH:21][CH:22]=[C:23]([F:24])[C:17]=3[C:16]=2[Cl:25])[CH3:13])=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 16659815HCID 16659815, compound

Product 1

HCID 16659814HCID 16659814, compoundYield 201.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of (E)-3-(6-amino-pyridin-3-yl)-N-(3-chloro-4-fluoro-benzo[b]thiophen-2-ylmethyl)-N-methylacrylamide (257 mg, 0.68 mmol) in CH2Cl2 (10 mL) was treated with anhydrous HCl (0.68 mL of a 1.0 M solution in Et2O, 0.68 mmol). The mixture was stirred overnight at room temperature and then diluted with Et2O. The resulting solid was collected by filtration and then dried under vacuum at 50° C. for 2 d to give the title compound (282 mg, 98%) 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), 7.87-7.82 (m, 1H), 7.55-7.20 (m, 4H), 7.04-7.00 (m, 1H), 5.15-4.88 (m, 2H), 3.54 (br s, 1H), 3.22-2.97 (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. for 2 d

Sources & evidence

ORD record
ord-ef8c5eab318d4e2486bc8ccc5d04aadd
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

Loading…