Hydrochloric Acid → HCID 67085478, compound

HRID 2036712Notes

Reaction equation

HRID 2036712 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([C:14]1[CH:22]=[CH:21][C:20]2[N:19]([CH3:23])[C:18]3[CH2:24][CH:25]4[NH:29][CH:28]([C:17]=3[C:16]=2[C:15]=1C(OC(C)(C)C)=O)[CH2:27][CH2:26]4)(=[O:13])=[O:12].[ClH:37]>C(OCC)C>[ClH:37].[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH3:23])[C:18]1[CH2:24][CH:25]3[NH:29][CH:28]([C:17]2=1)[CH2:27][CH2:26]3)(=[O:12])=[O:13]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67085645HCID 67085645, compound

Product 1

HCID 67085478HCID 67085478, compound

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) 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-(2-napthyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (41 mg, 45%, AUC HPLC >99%) as an off-white solid: mp 220-222° C.; 1H NMR (DMSO-d6, 300 MHz) δ 9.42 (br s, 1H), 9.16 (br s, 1H), 8.66 (d, J=1.5 Hz, 1H), 8.43 (d, J=1.5 Hz, 1H), 8.19 (dd, J=8.0 Hz, 2.1 Hz, 1H), 8.08 (d, J=8.7 Hz, 1H), 8.01 (dd, J=8.0 Hz, 2.1 Hz, 1H), 7.88 (dd, J=8.7 Hz, 2.1 Hz, 1H), 7.64-7.75 (m, 4H), 5.36 (d, J=3.9 Hz, 1H), 4.47 (br s, 1H), 3.67 (s, 3H), 3.30-3.42 (m, 1H), 3.00 (d, J=17.1 Hz, 1H), 2.18-2.34 (m, 2H), 2.05-2.15 (m, 1H), 1.70-1.87 (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-fc3832e4f19840fbb88c8a0885d934f5
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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