Trifluoroacetic acid → HCID 87262770, compound

HRID 2036698Notes

Reaction equation

[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([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:6]=[CH:7][CH:8]=1.[C:37]([OH:43])([C:39]([F:42])([F:41])[F:40])=[O:38]>>[F:40][C:39]([F:42])([F:41])[C:37]([OH:43])=[O:38].[F:35][C:2]([F:1])([F:36])[C:3]1[CH:4]=[C:5]([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:10])=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 67085636HCID 67085636, compound

Product 1

HCID 87262770HCID 87262770, compoundYield 95%

Procedure

The product of step A was subjected to Boc-deprotection with TFA following the procedure of Example 28, step B. The crude material was purified by flash column chromatography (SiO2, 9:1 dichloromethane/methanol) to give 2-(3-trifluoromethylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole trifluoroacetate (130 mg, 95%) as a white solid: 1H NMR (CDCl3, 300 MHz) δ 8.20 (s, 1H), 8.10-8.14 (m, 2H), 7.57-7.78 (m, 3H), 7.33 (d, J=8.7 Hz 1H), 4.89 (d, J=4.5 Hz, 1H), 4.30-4.34 (m, 1H), 3.60 (s, 3H), 3.40 (dd, J=12.0, 4.5 Hz, 1H), 2.65 (d, J=16.8 Hz, 1H), 2.30-2.39 (m, 2H), 2.08-2.16 (m, 1H), 1.66-1.72 (m, 1H).

Workup

customThe crude material was purified by flash column chromatography (SiO2, 9:1 dichloromethane/methanol)

Sources & evidence

ORD record: ord-285499ebb5344de78f021cbdf7f976ae
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575186B2

Reaction notes

Loading…