Hydrochloric Acid → HCID 67085675, compound

HRID 2036748Notes

Reaction equation

HRID 2036748 reaction equation
[C:1]1([S:7]([C:10]2[CH:18]=[CH:17][C:16]3[N:15]([CH:19]([CH3:21])[CH3:20])[C:14]4[CH2:22][CH:23]5[NH:27][CH:26]([C:13]=4[C:12]=3[C:11]=2C(OC(C)(C)C)=O)[CH2:25][CH2:24]5)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:35]>ClCCl.C(OCC)C>[ClH:35].[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH:19]([CH3:21])[CH3:20])[C:14]2[CH2:22][CH:23]4[NH:27][CH:26]([C:13]3=2)[CH2:25][CH2:24]4)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67085665HCID 67085665, compound

Product 1

HCID 67085675HCID 67085675, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of step B (100 mg, 0.06 mmol) in dichloromethane was added 2M HCl in diethylether (2 mL). After stirring at ambient temperature for 5 h the reaction mixture was concentrated in vacuo, triturated with ethyl acetate and lyophilized from water to give 2-phenylsulfonyl-5-isopropyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (50 mg, 57%, AUC HPLC >99%) as a white solid: mp 260-265° C., 1H NMR (CD3OD, 300 MHz) δ 8.26 (d, J=1.5 Hz, 1H), 7.93-7.97 (m, 2H), 7.67-7.76 (m, 2H), 7.51-7.59 (m, 3H), 5.28-5.30 (m, 1H), 4.69-4.75 (m, 1H), 4.52 (br s, 1H), 3.55 (dd, J=17.2, 5.1 Hz, 1H), 3.11 (d, J=17.4 Hz, 1H), 2.28-2.43 (m, 3H), 1.93-2.02 (m, 1H), 1.59 (d, J=7.2 Hz, 3H), 1.56 (d, J=6.9 Hz, 3H); ESI, m/z 381 [M+H]+.

Workup

  1. concentrationwas concentrated in vacuo
  2. customtriturated with ethyl acetate

Sources & evidence

ORD record
ord-8280b978199e4bb48d926b9605aad4f3
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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