Hydrochloric Acid → HCID 68108635, compound

HRID 2179396Notes

Reaction equation

HRID 2179396 reaction equation
[Cl:1][C:2]1[C:7]2[O:8][C:9]3[CH2:14][CH:13]([CH3:15])[NH:12][CH2:11][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][CH:13]([CH3:15])[NH:12][CH2:11][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 68108636HCID 68108636, compound

Product 1

HCID 68108635HCID 68108635, compoundYield 180.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

6-chloro-3-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-3-methyl-8-(phenylsulfonyl)-1,2,3,4-tetra hydrobenzofuro[3,2-c]pyridine hydrochloride (81b, 108 mg, 96%, AUC HPLC 98.1%): mp <<MP data>>; 1H NMR (DMSO-d6, 400 MHz) δ 9.62 (br, 2H), 8.41 (d, J=1.6 Hz, 1H), 8.04-8.02 (m, 3H), 7.71-7.62 (m, 3H), 4.51-4.32 (m, 2H), 3.77-3.72 (m, 1H), 3.26-3.24 (m, 1H), 2.98-2.91 (m, 1H), 1.44 (d, J=6.4 Hz, 3H); ESI MS m/z 403 [M+H+CH3CN]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-0268978d04b54bb8b30c479e9d677631
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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