Hydrochloric Acid → HCID 67085143, compound

HRID 2036752Notes

Reaction equation

HRID 2036752 reaction equation
[C:1]1([S:7]([C:10]2[CH:18]=[CH:17][C:16]3[N:15]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:14]4[CH2:25][CH:26]5[NH:30][CH:29]([C:13]=4[C:12]=3[C:11]=2C(OC(C)(C)C)=O)[CH2:28][CH2:27]5)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:38]>CO.C(OCC)C>[ClH:38].[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:14]2[CH2:25][CH:26]4[NH:30][CH:29]([C:13]3=2)[CH2:28][CH2:27]4)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67173431HCID 67173431, compound

Product 1

HCID 67085143HCID 67085143, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of the product of step D (70 mg, 0.13 mmol) in methanol was added 2M HCl in diethylether (4 mL). After stirring for 2 h, the solution was concentrated in vacuo, triturated with ethyl acetate, and lyophilized from water to give 2-phenylsulfonyl-5-phenyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (50 mg, 57%, AUC HPLC >99%) as a white solid: mp 195-200° C.; 1H NMR (CD3OD, 300 MHz) δ 8.38 (d, J=1.8 Hz, 1H), 7.95-7.99 (m, 2H), 7.72 (dd, J=8.8, 1.5 Hz, 1H), 7.51-7.64 (m, 6H), 7.39-7.42 (m, 2H), 7.32 (d, J=9.0 Hz, 1H), 5.39-5.40 (m, 1H), 4.49 (br s, 1H), 3.39 (dd, J=8.7, 4.5 Hz, 1H), 2.81 (d, J=17.7 Hz, 1H), 2.37-2.46 (m, 3H), 1.98-2.08 (m, 1H); ESI, m/z 415 [M+H]+.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. customtriturated with ethyl acetate

Sources & evidence

ORD record
ord-ed8a1cf9b6674a49b1a194b38df2a622
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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