Hydrochloric Acid → HCID 68109254, compound

HRID 2179380Notes

Reaction equation

HRID 2179380 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[C:12]([CH2:23][OH:24])[C:13]3[O:22][C:21]4[CH2:20][CH2:19][NH:18][CH2:17][C:16]=4[C:14]=3[CH:15]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:25]>ClCCl.CO>[ClH:25].[C:1]1([S:7]([C:10]2[CH:11]=[C:12]([CH2:23][OH:24])[C:13]3[O:22][C:21]4[CH2:20][CH2:19][NH:18][CH2:17][C:16]=4[C:14]=3[CH:15]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68108531HCID 68108531, compound

Product 1

HCID 68109254HCID 68109254, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

The product obtained in step G (14 mg, 0.04 mmol) was converted to the 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-(phenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridin-6-yl)methanol hydrochloride (15 mg, 97%, AUC HPLC>99%) as a white solid: mp <<MP data>>; 1H NMR (DMSO-d6, 400 MHz) δ 9.32 (br s, 2H), 8.30 (d, J=1.2 Hz, 1H), 7.99-7.87 (m, 3H), 7.71-7.57 (m, 3H), 5.58 (t, J=5.6 Hz, 1H), 4.81 (d, J=5.6 Hz, 2H), 4.38 (s, 2H), 3.52 (t, J=6.0 Hz, 2H), 3.17-3.05 (m, 2H); ESI MS m/z 344 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-b40a7204617c4938bbebd7109d3055a0
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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