Trifluoroacetic acid → HCID 67085368, compound

HRID 2036741Notes

Reaction equation

HRID 2036741 reaction equation
[C:1]1([S:7]([C:10]2[CH:18]=[C:17]([Cl:19])[C:16]3[N:15]([CH3:20])[C:14]4[CH2:21][CH:22]5[NH:26][CH:25]([C:13]=4[C:12]=3[C:11]=2C(OC(C)(C)C)=O)[CH2:24][CH2:23]5)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>>[ClH:19].[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:16](=[C:17]([Cl:19])[CH:18]=2)[N:15]([CH3:20])[C:14]2[CH2:21][CH:22]4[NH:26][CH:25]([C:13]3=2)[CH2:24][CH2:23]4)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67085431HCID 67085431, compound

Product 1

HCID 67085368HCID 67085368, compound

Procedure

The product of step F was subjected to Boc-deprotection with TFA following the procedure of Example 28, step B. The crude free base was purified by flash column chromatography (SiO2, 90:9:1 dichloromethane/methanol/ammonium hydroxide) and the product treated directly with 1.25 M HCl in methanol. The solution was concentrated in vacuo to give 2-phenylsulfonyl-4-chloro-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (123 mg, 97%, HPLC, AUC >99%.) as a white solid: mp 258-264° C. dec; 1H NMR (DMSO-d6, 300 MHz): δ 9.70 (br s, 1H), 9.20 (br s, 1H), 8.38 (d, J=1.2 Hz, 1H), 7.94-8.02 (m, 2H), 7.58-7.69 (m, 4H), 5.37 (d, J=3.3 Hz, 1H), 4.42-4.57 (m, 1H), 3.82 (s, 3H), 3.30-3.40 (m, 1H), 3.00 (d, J=12.6 Hz, 1H), 2.20-2.33 (m, 2H), 2.03-2.12 (m, 1H), 1.73-1.86 (m, 1H); ESI MS m/z 387 [M+H]+

Workup

  1. customThe crude free base was purified by flash column chromatography (SiO2, 90:9:1 dichloromethane/methanol/ammonium hydroxide)
  2. additionthe product treated directly with 1.25 M HCl in methanol
  3. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-19f44d69b1e740309e3638fd535fa8da
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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