Hydrochloric Acid → 2-(4-Methoxyphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride

HRID 2036688Notes

Reaction equation

HRID 2036688 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[CH:20]=[CH:19][C:18]3[N:17]([CH3:21])[C:16]4[CH2:22][CH:23]5[NH:27][CH:26]([C:15]=4[C:14]=3[C:13]=2C(OC(C)(C)C)=O)[CH2:25][CH2:24]5)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[ClH:35]>C(OCC)C>[ClH:35].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([CH3:21])[C:16]2[CH2:22][CH:23]4[NH:27][CH:26]([C:15]3=2)[CH2:25][CH2:24]4)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67085572Tert-butyl 2-(4-methoxyphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

Product 1

HCID 529129802-(4-Methoxyphenyl)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 B. The crude material was purified by flash column chromatography (SiO2, 80:18:2 chloroform/methanol/ammonium hydroxide) and the product treated directly with 1.25 M HCl in methanol (0.5 mL). After concentration in vacuo the residue was lyophilized to give 2-(4-methoxyphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (49 mg, 34%, AUC HPLC 98.0%) as a light-yellow solid: mp 210-212° C.; 1H NMR (DMSO-d6, 300 MHz) δ 9.34 (br s, 1H), 9.04 (br s, 1H), 8.32 (s, 1H), 7.85 (dd, J=7.2, 2.1 Hz, 2H), 7.63 (s, 2H), 7.09 (dd, J=7.2, 2.1 Hz, 2H), 5.35 (d, J=3.9 Hz, 1H), 4.48 (br s, 1H), 3.80 (s, 3H), 3.67 (s, 3H), 3.35-3.45 (m, 1H), 3.01 (d, J=17.1 Hz, 1H), 2.18-2.33 (m, 2H), 2.04-2.15 (m, 1H), 1.72-1.86 (m, 1H); ESI MS m/z 383 [M+H]+.

Workup

  1. customThe crude material was purified by flash column chromatography (SiO2, 80:18:2 chloroform/methanol/ammonium hydroxide)
  2. additionthe product treated directly with 1.25 M HCl in methanol (0.5 mL)
  3. concentrationAfter concentration in vacuo the residue

Sources & evidence

ORD record
ord-3cc1da2c836745a49d7a05213b2fffd8
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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