Hydrochloric Acid → HCID 67085220, compound

HRID 2036739Notes

Reaction equation

HRID 2036739 reaction equation
[C:1]1([S:7]([C:10]2[CH:18]=[C:17]([F:19])[C:16]3[N:15]([CH3:20])[C:14]4[CH2:21][CH:22]5[NH:26][CH:25]([C:13]=4[C:12]=3[C:11]=2C(OC(C)(C)C)=O)[CH2:24][CH2:23]5)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:34]>C(OCC)C>[ClH:34].[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:16](=[C:17]([F:19])[CH:18]=2)[N:15]([CH3:20])[C:14]2[CH2:21][CH:22]4[NH:26][CH:25]([C:13]3=2)[CH2:24][CH2:23]4)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67085359HCID 67085359, compound

Product 1

HCID 67085220HCID 67085220, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The product of step D was subjected to Boc-deprotection with 2 N HCl in diethyl ether following the procedure of Example 28, step B. The crude material was purified by flash column chromatography (90:9:1 dichloromethane/methanol/ammonium hydroxide) to give 2-phenylsulfonyl-4-fluoro-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (40 mg, 84%, HPLC, AUC 97.8%.) as a white solid: mp 251-256° C. dec; 1H NMR (DMSO-d6, 300 MHz): δ 8.24 (d, J=1.5 Hz, 1H), 7.94-8.00 (m, 2H), 7.56-7.70 (m, 3H), 7.48 (dd, J=12.0, 1.5 Hz, 1H), 5.36 (d, J=3.9 Hz, 1H), 4.44-4.52 (m, 1H), 3.82 (s, 3H), 3.34-3.39 (m, 1H), 3.00 (d, J=17.1 Hz, 1H), 2.18-2.30 (m, 2H), 2.03-2.12 (m, 1H), 1.70-1.87 (m, 1H); APCI MS m/z 371 [M+H]+

Workup

  1. customThe crude material was purified by flash column chromatography (90:9:1 dichloromethane/methanol/ammonium hydroxide)

Sources & evidence

ORD record
ord-60dc074f05d647daab7f71c65a047ce5
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

Loading…