Hydrochloric Acid → HCID 52912974, compound

HRID 2036682Notes

Reaction equation

HRID 2036682 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH3:20])[C:15]2[CH2:21][CH:22]4[NH:26][CH:25]([C:14]3=2)[CH2:24][CH2:23]4)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[ClH:27]>CO>[ClH:27].[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH3:20])[C:15]2[CH2:21][CH:22]4[NH:26][CH:25]([C:14]3=2)[CH2:24][CH2:23]4)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 52912975HCID 52912975, compound

Product 1

HCID 52912974HCID 52912974, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product of step B was treated with 1.25 M HCl in methanol (2 mL). The solution was concentrated in vacuo, dissolved in water and washed with dichloromethane. The aqueous layer was lyophilized to give 2-(4-fluorophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (25 mg, 73%, AUC HPLC 95.9%) as a white solid: mp 210-214° C.; 1H NMR (CD3OD, 300 MHz) δ 8.27 (s, 1H), 7.99-8.03 (m, 2H), 7.72 (d, J=8.4 Hz, 1H), 7.57 (d, J=7.1 Hz, 1H), 7.24-7.30 (m, 2H), 5.30 (d, J=4.5 Hz, 1H), 4.59 (br s, 1H), 3.72 (s, 3H), 3.48 (dd, J=12.6, 4.5 Hz, 1H), 3.07 (d, J=17.4 Hz, 1H), 2.24-2.47 (m, 3H), 1.95-2.00 (m, 1H); ESI MS m/z 371 [M+H]+.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutiondissolved in water
  3. washwashed with dichloromethane

Sources & evidence

ORD record
ord-ebc904197d8043f8a3d03f292cac15f6
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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