Hydrochloric Acid → HCID 68108910, compound

HRID 2179395Notes

Reaction equation

HRID 2179395 reaction equation
[Cl:1][C:2]1[C:7]2[O:8][C:9]3[CH2:14][CH2:13][NH:12][CH:11]([CH3:15])[C:10]=3[C:6]=2[CH:5]=[C:4]([S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:3]=1.Cl>CO>[ClH:1].[Cl:1][C:2]1[C:7]2[O:8][C:9]3[CH2:14][CH2:13][NH:12][CH:11]([CH3:15])[C:10]=3[C:6]=2[CH:5]=[C:4]([S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68108832HCID 68108832, compound

Product 1

HCID 68108910HCID 68108910, compoundYield 184.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

6-chloro-1-methyl-8-(phenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine (100 mg, 0.3 mmol) was converted to the hydrochloride salt by dissolving in methanol and treating with 1.25 M HCl in methanol. The reaction mixture was concentrated in vacuo to give 6-chloro-1-methyl-8-(phenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine hydrochloride (81a, 110 mg, 97%, AUC HPLC>99%): mp <<MP data>>; 1H NMR (DMSO-d6, 400 MHz) δ 9.55 (br s, 2H), 8.35 (d, J=1.6 Hz, 1H), 8.07-8.03 (m, 3H), 7.70-7.61 (m, 3H), 4.87-4.82 (m, 1H), 3.65-3.59 (m, 1H), 3.49-3.43 (m, 1H), 3.16-3.13 (m, 2H), 1.66 (d, J=6.8 Hz, 3H); ESI MS m/z 403 [M+H+CH3CN]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-fa1743b946b542b08dc115219c76ccd3
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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