Hydrochloric Acid → HCID 52913221, compound

HRID 2036703Notes

Reaction equation

HRID 2036703 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([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:6]=[CH:7][CH:8]=1.[ClH:35]>C(OCC)C>[ClH:35].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([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:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67085605HCID 67085605, compound

Product 1

HCID 52913221HCID 52913221, 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, 95:5 dichloromethane/methanol). The free base was dissolved in methanol (0.5 mL) and treated with 1.25 M HCl in methanol (1.5 mL). The solution was concentrated in vacuo to give 2-(3-methoxyphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (19 mg, 85%, AUC HPLC >99%) as an off-white solid: mp 186-190° C.; 1H NMR (CD3OD, 300 MHz) δ 8.27 (d, J=1.8 Hz 1H), 7.73 (dd, J=8.7, 1.8 Hz, 1H), 7.58 (d, J=8.7 Hz, 1H), 7.41-7.51 (m, 3H), 7.10-7.17 (m, 1H), 5.30 (d, J=4.8 Hz, 1H), 4.51-4.58 (m, 1H), 3.82 (s, 3H), 3.70 (s, 3H), 3.48 (dd, J=17.4, 4.5 Hz 1H), 2.25-2.47 (m, 3H), 2.16-2.23 (m, 1H), 1.94-2.23 (m, 1H). ESI MS m/z 383 [M+H]+

Workup

  1. customThe crude material was purified by flash column chromatography (SiO2, 95:5 dichloromethane/methanol)
  2. dissolutionThe free base was dissolved in methanol (0.5 mL)
  3. additiontreated with 1.25 M HCl in methanol (1.5 mL)
  4. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-3c65491941ef4dd5bec6ff1f02e0f606
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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