Trifluoroacetic acid → N-[2-[[(2,3-Difluorophenyl)methyl]thio]-6-[(1R)-2-hydroxy-1-methylethoxy]-4-pyrimidinyl]-4-methyl-piperazine-1-sulfonamide

HRID 2388822Notes

Reaction equation

HRID 2388822 reaction equation
[F:1][C:2]1[C:50]([F:51])=[CH:49][CH:48]=[CH:47][C:3]=1[CH2:4][S:5][C:6]1[N:11]=[C:10]([NH:12][S:13]([N:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)(=[O:15])=[O:14])[CH:9]=[C:8]([O:23][C@H:24]([CH3:46])[CH2:25][O:26]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[C:50]([F:51])=[CH:49][CH:48]=[CH:47][C:3]=1[CH2:4][S:5][C:6]1[N:11]=[C:10]([NH:12][S:13]([N:16]2[CH2:17][CH2:18][N:19]([CH3:22])[CH2:20][CH2:21]2)(=[O:14])=[O:15])[CH:9]=[C:8]([O:23][C@H:24]([CH3:46])[CH2:25][OH:26])[N:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53628375N-{2-[(2,3-difluorobenzyl)thio]-6-[(1R)-1-methyl-2-(trityloxy)ethoxy]pyrimidin-4-yl}-4-methylpiperazine-1-sulfonamide

Product 1

HCID 59558822N-[2-[[(2,3-Difluorophenyl)methyl]thio]-6-[(1R)-2-hydroxy-1-methylethoxy]-4-pyrimidinyl]-4-methyl-piperazine-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-{2-[(2,3-difluorobenzyl)thio]-6-[(1R)-1-methyl-2-(trityloxy)ethoxy]pyrimidin-4-yl}-4-methylpiperazine-1-sulfonamide (the product from step (100 mg) in DCM (3 ml) was added TFA (3 ml) dropwise. The reaction was then allowed to stir at room temperature for the following 3 h until complete. The reaction was then reduced in vacuo and the resulting residue was purified by preparative HPLC to yield the title compound as a white solid. Yield: 45 mg

Workup

  1. customthe resulting residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-329cf8ef30ec4641871121e47f26ee4e
Source dataset
uspto-grants-2012_09
Patent number
US08269002B2

Reaction notes

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