Hydrochloric Acid → HCID 68109140, compound

HRID 2179368Notes

Reaction equation

HRID 2179368 reaction equation
C(OC([N:6]1[C:14]2[C:9](=[CH:10][C:11]([S:15]([C:18]3[CH:19]=[C:20]([O:38][CH3:39])[C:21]4[O:30][C:29]5[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][C:24]=5[C:22]=4[CH:23]=3)(=[O:17])=[O:16])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)=O)C.[ClH:40]>ClCCl.CO>[ClH:40].[NH:6]1[C:14]2[C:9](=[CH:10][C:11]([S:15]([C:18]3[CH:19]=[C:20]([O:38][CH3:39])[C:21]4[O:30][C:29]5[CH2:28][CH2:27][NH:26][CH2:25][C:24]=5[C:22]=4[CH:23]=3)(=[O:17])=[O:16])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 70565636HCID 70565636, compound

Product 1

HCID 68109140HCID 68109140, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

The product obtained in step D (10 mg, 0.02 mmol) was converted to 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-((1H-indol-5-yl)sulfonyl)-6-methoxy-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine hydrochloride (7 mg, 64%, AUC HPLC 97.6%) as a white solid: mp <<MP data>>; 1H NMR (DMSO-d6, 400 MHz) δ 11.64 (s, 1H), 9.20 (br s, 2H), 8.27 (d, J=2.0 Hz, 1H), 7.93 (d, J=1.6 Hz, 1H), 7.66 (dd, J=8.8, 2.0 Hz, 1H), 7.59-7.51 (m, 2H), 7.43 (d, J=1.6 Hz, 1H), 6.67-6.61 (m, 1H), 4.35 (s, 2H), 4.00 (s, 3H), 3.49 (t, J=6.0 Hz, 2H), 3.11-3.02 (m, 2H); ESI MS m/z 383 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-693f4c69844e46b0acd651c520e924db
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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