Hydrochloric Acid → HCID 68109631, compound

HRID 2179423Notes

Reaction equation

HRID 2179423 reaction equation
[Cl:1][C:2]1[C:7]2[O:8][C:9]3[CH2:14][CH2:13][NH:12][CH:11]([C:15]([N:17]([CH3:19])[CH3:18])=[O:16])[C:10]=3[C:6]=2[CH:5]=[C:4]([S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:22])=[O:21])[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]([C:15]([N:17]([CH3:19])[CH3:18])=[O:16])[C:10]=3[C:6]=2[CH:5]=[C:4]([S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68108826HCID 68108826, compound

Product 1

HCID 68109631HCID 68109631, compoundYield 219.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The product of step C (60 mg, 0.12 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-N,N-dimethyl-8-(phenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine-1-carboxamide hydrochloride (60 mg, 94%, AUC HPLC>99%) as an off-white solid: mp <<MP data>>; 1H NMR (CD3OD, 400 MHz) δ 7.92-7.90 (m, 3H), 7.77-7.76 (m, 1H), 7.56-7.48 (m, 3H), 5.03 (s, 1H), 3.52-3.46 (m, 1H), 3.40 (s, 3H), 3.18-3.12 (m, 1H), 3.08 (s, 3H), 2.93-2.77 (m, 2H); ESI MS m/z 419 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-78d1954ea9c04d5eb1af429236d0f084
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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