Hydrochloric Acid → HCID 68109152, compound

HRID 2179329Notes

Reaction equation

HRID 2179329 reaction equation
[C:1]1([S:11]([C:14]2[CH:15]=[CH:16][C:17]3[O:26][C:25]4[CH2:24][CH2:23][NH:22][CH2:21][C:20]=4[C:18]=3[CH:19]=2)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[ClH:27]>CO>[ClH:27].[C:1]1([S:11]([C:14]2[CH:15]=[CH:16][C:17]3[O:26][C:25]4[CH2:24][CH2:23][NH:22][CH2:21][C:20]=4[C:18]=3[CH:19]=2)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68108945HCID 68108945, compound

Product 1

HCID 68109152HCID 68109152, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The product of step B 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 8-(1-naphthylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine hydrochloride (52 mg, 100%, AUC HPLC 94.5%) as a white solid: mp 200-202° C.; 1H NMR (DMSO-d6, 300 MHz) δ 9.51 (br s, 2H), 8.61-8.45 (m, 3H), 8.33 (d, J=8.1 Hz, 1H), 8.14-8.05 (m, 1H), 7.87 (dd, J=8.7, 2.1 Hz, 1H), 7.82-7.74 (m, 2H), 7.69-7.57 (m, 2H), 4.39 (s, 2H), 3.58-3.45 (m, 2H), 3.10 (t, J=5.7 Hz, 2H); ESI MS m/z 364 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-3b20d1fddc94449f956cf473d96cddab
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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