Hydrochloric Acid → HCID 67085735, compound

HRID 2036727Notes

Reaction equation

HRID 2036727 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([S:13]([C:16]3[CH:24]=[CH:23][C:22]4[N:21]([CH3:25])[C:20]5[CH2:26][CH:27]6[NH:31][CH:30]([C:19]=5[C:18]=4[C:17]=3C(OCCCC)=O)[CH2:29][CH2:28]6)(=[O:15])=[O:14])[CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:39]>C(O)C>[ClH:39].[C:1]1([C:7]2[CH:8]=[C:9]([S:13]([C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[N:21]([CH3:25])[C:20]3[CH2:26][CH:27]5[NH:31][CH:30]([C:19]4=3)[CH2:29][CH2:28]5)(=[O:14])=[O:15])[CH:10]=[CH:11][CH:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131731026HCID 131731026, compound

Product 1

HCID 67085735HCID 67085735, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the product of step A (0.30 g, 0.56 mmol) in ethanol (20 mL) was added concentrated HCl (8.0 mL). The reaction mixture was stirred at ambient temperature overnight then concentrated in vacuo. The residue was purified by semi-preparative HPLC. The free base was dissolved in methanol and treated with concentrated HCl then concentrated to dryness in vacuo to give 2-[(3-phenyl)-phenyl]sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (98 mg, 38%, AUC HPLC 97.7%) as a light brown solid: mp 230-235° C. dec; 1H NMR (CDCl3, 300 MHz) δ 9.71 (s, 1H), 9.12 (s, 1H), 8.45 (d, J=1.2 Hz, 1H), 8.15 (t, J=1.2 Hz, 1H), 7.89-7.94 (m, 2H), 7.75 (dd, J=6.6, 1.2 Hz, 1H), 7.63-7.71 (m, 4H), 7.48-7.53 (m, 2H), 7.40-7.46 (m, 1H), 5.36 (d, J=3.0 Hz, 1H), 4.45 (br s, 1H), 3.67 (s, 3H), 3.37 (dd, J=12.9, 3.3 Hz, 1H), 2.99 (d, J=12.9 Hz, 1H), 2.23-2.31 (m, 2H), 1.99-2.11 (m, 1H), 1.74-1.81 (m, 1H); ESI MS m/z 429 [M+H]+.

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was purified by semi-preparative HPLC
  3. dissolutionThe free base was dissolved in methanol
  4. additiontreated with concentrated HCl
  5. concentrationthen concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-b5247ef32cb74198ad82746588207345
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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