Trifluoroacetic acid methylene chloride → HCID 68716636, compound

HRID 1159806Notes

Reaction equation

HRID 1159806 reaction equation
[OH:1][C:2]1[C:3]([CH2:20][N:21]2[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]2)=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:6]=[CH:5]2.C(Cl)Cl.[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].[C:14]1([S:11]([N:7]2[C:8]3[C:4](=[C:3]([CH2:20][N:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)[C:2]([OH:1])=[CH:10][CH:9]=3)[CH:5]=[CH:6]2)(=[O:13])=[O:12])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 86618251HCID 86618251, compound

Product 1

HCID 68716636HCID 68716636, compoundYield 53%

Procedure

tert-Butyl 4-{[5-hydroxy-1-(phenylsulfonyl)-1H-indol-4-yl]methyl}piperazine-1-carboxylate, (10 mg, 0.018 mmol, Intermediate 64) was dissolved in DCM/TFA 50/50 (1 mL) and left in RT for 4 hours after which time the solvent was removed at reduced pressure and the residue was purified on a preparative HPLC, Method A, to yield 5.5 mg (53%) of the target compound as a colourless oil. MS (ESI+) for C19H21N3O3S m/z 372 (M+H)+.

Workup

  1. customwas removed at reduced pressure
  2. customthe residue was purified on a preparative HPLC, Method A

Sources & evidence

ORD record
ord-162bffe45e5c472fb331aeaf50b3bb4f
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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