Hydrochloric Acid → HCID 68109183, compound

HRID 2179331Notes

Reaction equation

HRID 2179331 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([C:14]1[CH:15]=[CH:16][C:17]2[O:26][C:25]3[CH2:24][CH2:23][NH:22][CH2:21][C:20]=3[C:18]=2[CH:19]=1)(=[O:13])=[O:12].[ClH:27]>C(Cl)(Cl)Cl.CO>[ClH:27].[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([C:14]1[CH:15]=[CH:16][C:17]2[O:26][C:25]3[CH2:24][CH2:23][NH:22][CH2:21][C:20]=3[C:18]=2[CH:19]=1)(=[O:12])=[O:13]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68109184HCID 68109184, compound

Product 1

HCID 68109183HCID 68109183, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

The product of step B (50 mg, 0.10 mmol) was converted to hydrochloride salt by dissolving in chloroform and treating with 1.25 M HCl in methanol. The reaction mixture was concentrated in vacuo to give 8-(2-naphthylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine hydrochloride (52 mg, 95%, AUC HPLC>99%) as a white solid: mp 267-270° C.; 1H NMR (DMSO-d6, 300 MHz) δ 9.58 (br s, 2H), 8.71 (s, 1H), 8.45 (d, J=1.8 Hz, 1H), 8.24-8.17 (m, 1H), 8.12 (d, J=8.7 Hz, 1H), 8.06-7.88 (m, 3H), 7.82 (d, J=8.7 Hz, 1H), 7.77-7.65 (m, 2H), 4.39 (s, 2H), 3.57-3.47 (m, 2H), 3.16-3.06 (m, 2H); ESI MS m/z 364 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-0261862e8e1b40889eb2cd412712e45a
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

Loading…