Hydrochloric Acid → HCID 68108558, compound

HRID 2179327Notes

Reaction equation

HRID 2179327 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([C:12]2[CH:13]=[CH:14][C:15]3[O:24][C:23]4[CH2:22][CH2:21][NH:20][CH2:19][C:18]=4[C:16]=3[CH:17]=2)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl>CO>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([C:12]2[CH:13]=[CH:14][C:15]3[O:24][C:23]4[CH2:22][CH2:21][NH:20][CH2:19][C:18]=4[C:16]=3[CH:17]=2)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68108559HCID 68108559, compound

Product 1

HCID 68108558HCID 68108558, compoundYield 191.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The product of step B (30 mg, 0.08 mmol) was converted to hydrochloride salt by dissolving in methanol and treating with 1.25 M HCl in methanol. The reaction mixture was concentrated in vacuo to give 8-(3,5-dichlorophenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine hydrochloride (32 mg, 98%, AUC HPLC 98.3%) as a white solid: mp 312-315° C.; 1H NMR (DMSO-d6, 300 MHz) δ 9.43 (br s, 2H), 8.50 (d, J=1.8 Hz, 1H), 8.06-7.96 (m, 4H), 7.86 (d, J=8.7 Hz, 1H), 4.40 (s, 2H), 3.54 (t, J=6.0 Hz, 2H), 3.17-3.07 (m, 2H); APCI MS m/z 382 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-f7e0ddd1ba6a424cb8cbbdf0a1f3a113
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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