Hydrochloric Acid → HCID 16659814, compound

HRID 2097049Notes

Reaction equation

HRID 2097049 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-220b80d8f1d9483682774d7d4b41fe53
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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