Trifluoroacetic acid methylene chloride → HCID 86624983, compound

HRID 1096497Notes

Reaction equation

HRID 1096497 reaction equation
[CH3:1][CH:2]1[C:13]2[C:14]3[C:6](=[CH:7][N:8]([S:23]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)(=[O:25])=[O:24])[C:9]=3[CH:10]=[CH:11][C:12]=2[O:15][S:16]([C:19]([F:22])([F:21])[F:20])(=[O:18])=[O:17])[CH2:5][CH2:4][N:3]1C(OC(C)(C)C)=O.C(Cl)Cl.[C:42]([OH:48])([C:44]([F:47])([F:46])[F:45])=[O:43]>>[F:45][C:44]([F:47])([F:46])[C:42]([OH:48])=[O:43].[F:21][C:19]([F:20])([F:22])[S:16]([O:15][C:12]1[CH:11]=[CH:10][C:9]2[N:8]([S:23]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)(=[O:24])=[O:25])[CH:7]=[C:6]3[CH2:5][CH2:4][NH:3][CH:2]([CH3:1])[C:13]=1[C:14]=23)(=[O:17])=[O:18]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 59848829HCID 59848829, compound

Product 1

HCID 86624983HCID 86624983, compound

Procedure

tert-Butyl 6-methyl-1-(phenylsulfonyl)-7-{[(trifluoromethyl)sulfonyl]oxy}-1,3,4,6-tetrahydro-5H-azepino[5,4,3-cd]indole-5-carboxylate, Intermediate 16 (12.6 mg, 0.022 mmol) was dissolved in a 50/50 mixture of DCM/TFA (1 mL) and left at room temperature for one hour. The evaporated crude product was purified by preparative HPLC (ACE C8 5 mm, water containing 0.1% TFA —CH3CN) to give 7.2 mg of the title compound as a light brown oil. MS m/z 474 [M+H]+.

Workup

  1. customThe evaporated crude product
  2. customwas purified by preparative HPLC (ACE C8 5 mm, water containing 0.1% TFA —CH3CN)

Sources & evidence

ORD record
ord-7f4a36cc434d444194fdd1129444cee0
Source dataset
uspto-grants-2012_03
Patent number
US08138333B2

Reaction notes

Loading…