Hydrochloric Acid → HCID 67085565, compound

HRID 2036723Notes

Reaction equation

HRID 2036723 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([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]=[C:6]([F:8])[CH:7]=1.[ClH:35]>ClCCl.CO.C(OCC)C>[ClH:35].[F:8][C:6]1[CH:5]=[C:4]([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:3]=[C:2]([F:1])[CH:7]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 67173587HCID 67173587, compound

Product 1

HCID 67085565HCID 67085565, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of step A in dichloromethane (0.9 mL) and methanol (0.1 mL) was added 2M HCl in diethyl ether (5 mL). The reaction mixture was stirred at ambient temperature overnight, filtered, washed with diethyl ether and dried in vacuo to give 2-(3,5-difluorophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (15 mg, 50%, AUC HPLC 98.0%) as an off-white solid: mp 230-235° C. dec; 1H NMR (CD3OD, 300 MHz) δ 8.32 (d, J=1.8 Hz, 1H), 7.77 (dd, J=8.7, 1.8 Hz, 1H), 7.57-7.61 (m, 3H), 7.20-7.28 (m, 1H), 5.32 (d, J=4.8 Hz, 1H), 4.55 (br s, 1H), 3.73 (s, 3H), 3.49 (dd, J=17.4, 4.5 Hz, 1H), 3.25-3.40 (m, 1H), 3.08 (d, J=17.4 Hz, 1H), 2.26-2.48 (m, 2H), 1.96-2.00 (m, 1H); ESI MS m/z 389 [M+H]+.

Workup

  1. filtrationfiltered
  2. washwashed with diethyl ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-0864a8c65a5d444a87dd8769ac38224d
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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