Hydrochloric Acid → 2-(1-Napthyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride

HRID 2036710Notes

Reaction equation

HRID 2036710 reaction equation
[C:1]1([S:11]([C:14]2[CH:22]=[CH:21][C:20]3[N:19]([CH3:23])[C:18]4[CH2:24][CH:25]5[NH:29][CH:28]([C:17]=4[C:16]=3[C:15]=2C(OC(C)(C)C)=O)[CH2:27][CH2:26]5)(=[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:37]>C(OCC)C>[ClH:37].[C:1]1([S:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[N:19]([CH3:23])[C:18]2[CH2:24][CH:25]4[NH:29][CH:28]([C:17]3=2)[CH2:27][CH2:26]4)(=[O:12])=[O:13])[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 67085781Tert-butyl 2-(1-napthyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

Product 1

HCID 670851702-(1-Napthyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The product of step A was subjected to Boc-deprotection with 2 M HCl in diethyl ether following the procedure of Example 28, step C. The crude material was purified by flash column chromatography (SiO2, 80:18:2 chloroform/methanol/ammonium hydroxide) followed by semi-preparative HPLC. The free base was treated with 1.25 M HCl in methanol (0.5 mL) and lyophilized to give 2-(1-napthyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (5 mg, 12%, AUC HPLC 97.9%) as a white solid: mp 229-231° C.; 1H NMR (DMSO-d6, 300 MHz) δ 9.38 (br s, 1H), 9.02 (br s, 1H), 8.63 (d, J=8.7 Hz, 1H), 8.48 (s, 1H), 8.43 (dd, J=7.2, 1.2 Hz, 1H), 8.28 (d, J=8.1 Hz, 1H), 8.03-8.09 (m, 1H), 8.76 (t, J=7.8 Hz, 1H), 7.57-7.65 (m, 4H), 5.38 (d, J=3.9 Hz, 1H), 4.47 (br s, 1H), 3.64 (s, 3H), 3.34-3.40 (m, 1H), 2.49 (d, J=17.4 Hz, 1H), 2.18-2.33 (m, 2H), 2.03-2.12 (m, 1H), 1.71-1.89 (m, 1H); ESI MS m/z 403 [M+H]+.

Workup

  1. customThe crude material was purified by flash column chromatography (SiO2, 80:18:2 chloroform/methanol/ammonium hydroxide)
  2. additionThe free base was treated with 1.25 M HCl in methanol (0.5 mL)

Sources & evidence

ORD record
ord-bfe7e73012ee453f8ef43429a43b3c21
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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