Hydrochloric Acid → HCID 52913227, compound

HRID 2036708Notes

Reaction equation

HRID 2036708 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([C:13]2[CH:21]=[CH:20][C:19]3[N:18]([CH3:22])[C:17]4[CH2:23][CH:24]5[NH:28][CH:27]([C:16]=4[C:15]=3[C:14]=2C(OC(C)(C)C)=O)[CH2:26][CH2:25]5)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[ClH:36]>C(OCC)C>[ClH:36].[NH2:1][C:4]1[CH:5]=[C:6]([S:10]([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([CH3:22])[C:17]2[CH2:23][CH:24]4[NH:28][CH:27]([C:16]3=2)[CH2:26][CH2:25]4)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67085522HCID 67085522, compound

Product 1

HCID 52913227HCID 52913227, 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, 96:4 dichloromethane/methanol). The free base was treated with 1.25 M HCl in methanol (1.5 mL). The solution was concentrated in vacuo and the residue lyophilized to give 2-(3-aminophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (14 mg, 91%, AUC HPLC >99%) as an off-white solid: mp 220-222° C.; 1H NMR (CD3OD, 300 MHz) δ 8.27 (d, J=1.5 Hz, 1H), 7.72 (dd, J=8.7, 1.5 Hz, 1H), 7.54-7.60 (m, 3H), 7.41-7.46 (m, 1H), 7.18 (dd, J=7.8, 1.5 Hz 1H), 5.30 (d, J=4.2 Hz, 1H), 4.50 (br s, 1H), 3.72 (s, 3H), 3.52 (dd, J=18.0, 6.0 Hz, 1H), 3.07 (d, J=17.4 Hz, 1H), 2.25-2.50 (m, 3H), 1.97-2.00 (m, 1H); ESI MS m/z 368 [M+H]+.

Workup

  1. customThe crude material was purified by flash column chromatography (SiO2, 96:4 dichloromethane/methanol)
  2. additionThe free base was treated with 1.25 M HCl in methanol (1.5 mL)
  3. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-d6c6c58cc0594ee79c92c441ba190a9a
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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