Hydrochloric Acid → HCID 68109101, compound

HRID 2179374Notes

Reaction equation

HRID 2179374 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:12]=[C:13]([C:24]#[N:25])[C:14]3[O:23][C:22]4[CH2:21][CH2:20][NH:19][CH2:18][C:17]=4[C:15]=3[CH:16]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[ClH:26]>ClCCl.CO>[ClH:26].[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:12]=[C:13]([C:24]#[N:25])[C:14]3[O:23][C:22]4[CH2:21][CH2:20][NH:19][CH2:18][C:17]=4[C:15]=3[CH:16]=2)(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68109102HCID 68109102, compound

Product 1

HCID 68109101HCID 68109101, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

The product obtained in step C (13 mg, 0.03 mmol) was converted to hydrochloride salt by dissolving in dichloromethane and treating with 1.25 M HCl in methanol. The reaction mixture was concentrated in vacuo to give 8-((3-fluorophenyl)sulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine-6-carbonitrile hydrochloride (13.5 mg, 95%, AUC HPLC>99%) as a white solid: mp <<MP data>>; 1H NMR (DMSO-d6, 400 MHz) δ 9.25 (br s, 2H), 8.76 (d, J=2.0 Hz, 1H), 8.59 (d, J=2.0 Hz, 1H), 7.97-7.86 (m, 2H), 7.75-7.66 (m, 1H), 7.64-7.55 (m, 1H), 4.39 (s, 2H), 3.53 (t, J=6.0 Hz, 2H), 3.22-3.12 (m, 2H); APCI MS m/z 357 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-2f10870d3f9e4414bda0533e53af90c4
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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