Hydrochloric Acid → HCID 68109744, compound

HRID 2179405Notes

Reaction equation

HRID 2179405 reaction equation
[Cl:1][C:2]1[C:7]2[O:8][C:9]3[CH2:14][CH2:13][NH:12][CH:11]([CH2:15][OH:16])[C:10]=3[C:6]=2[CH:5]=[C:4]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])[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]([CH2:15][OH:16])[C:10]=3[C:6]=2[CH:5]=[C:4]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68109281HCID 68109281, compound

Product 1

HCID 68109744HCID 68109744, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The product of step E (30 mg, 0.08 mmol) was converted to the hydrochloride salt by dissolving in methanol and treating with 1.25 M HCl in methanol. The reaction solution was concentrated in vacuo to afford (6-chloro-8-(phenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridin-1-yl)methanol hydrochloride (7 mg, 70%, AUC HPLC 98.5%) as a white solid: mp 185-187° C.; 1H NMR (DMSO-d6, 400 MHz) δ 9.75 (br s, 2H), 8.38 (d, J=2.0 Hz, 1H), 8.06-8.03 (m, 3H), 7.71-7.63 (m, 3H), 5.61 (t, J=4.8 Hz, 1H), 4.81 (s, 1H), 4.04-4.00 (m, 2H), 3.63-3.60 (m, 1H), 3.49-3.46 (m, 1H), 3.16 (br s, 2H); APCI MS m/z 378 [M+H]+.

Workup

  1. concentrationThe reaction solution was concentrated in vacuo

Sources & evidence

ORD record
ord-9d7905cbbe174b95abc36b1017f6fb70
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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