Trifluoroacetic acid → HCID 67085602, compound

HRID 2036721Notes

Reaction equation

HRID 2036721 reaction equation
[Cl: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]([Cl:8])[CH:7]=1.C(O)(C(F)(F)F)=O>>[ClH:1].[Cl: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]([Cl:1])[CH:7]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67173138HCID 67173138, compound

Product 1

HCID 67085602HCID 67085602, compound

Procedure

The product of step A was Boc-deprotected with TFA following the procedure of Example 28, Step B. The crude material was purified by flash column chromatography (SiO2, 90:9:1 dichloromethane/methanol/ammonium hydroxide) followed by semi-preparative HPLC. The free base was treated directly with 1.25 M HCl in methanol (2 mL) and the solution concentrated in vacuo to give 2-(3,5-dichlorophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (15 mg, 31%, AUC HPLC 98.9%) as an off-white solid: mp 190-195° C.; 1H NMR (CD3OD, 300 MHz) δ 8.32 (s, 1H), 7.88 (d, J=1.8 Hz, 2H), 7.58-7.78 (m, 3H), 5.28-5.38 (m, 1H), 4.55 (br s, 1H), 3.72 (s, 3H), 3.40-3.60 (m, 1H), 3.02-3.17 (m, 1H), 2.22-2.55 (m, 3H), 1.92-2.07 (m, 1H); ESI MS m/z 421 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-c202fb19916c4f929e7b044c5c200314
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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