Hydrochloric Acid → HCID 67085227, compound

HRID 2036726Notes

Reaction equation

HRID 2036726 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([S:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[C:13]2[CH2:19][CH:20]4[NH:24][CH:23]([C:12]3=2)[CH2:22][CH2:21]4)(=[O:8])=[O:7])=[CH:2]1.[ClH:25]>CO.ClCCl>[ClH:25].[S:1]1[CH:5]=[CH:4][C:3]([S:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[C:13]2[CH2:19][CH:20]4[NH:24][CH:23]([C:12]3=2)[CH2:22][CH2:21]4)(=[O:8])=[O:7])=[CH:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57392614HCID 57392614, compound

Product 1

HCID 67085227HCID 67085227, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of product from step B (25 mg, 0.07 mmol) in methanol (0.5 mL) and dichloromethane (0.5 mL) was added 1.25 M HCl in methanol (0.22 mL). The solution was concentrated in vacuo and the residue lyophilized to give 2-(3-thienyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (26 mg, 94%; AUC HPLC 98.5%) as a white solid. mp 208-212° C. dec; 1H NMR (DMSO-d6, 300 MHz) δ 9.56 (br s, 1H), 9.30 (br s, 1H), 8.30-8.39 (m, 2H), 7.63-7.76 (m, 3H), 7.39 (dd, J=5.1, 1.5 Hz, 1H), 5.31-5.39 (m, 1H), 4.42-4.52 (m, 1H), 3.68 (s, 3H), 3.31-3.44 (m, 1H), 3.01 (d, J=17.4 Hz, 1H), 2.20-2.36 (m, 2H), 2.01-2.14 (m, 1H), 1.72-1.89 (m, 1H); ESI, m/z 359 [M+H]+

Workup

  1. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-f7f73069817b400fad0e039c5e18e232
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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