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

HRID 1175455Notes

Reaction equation

HRID 1175455 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 ii) (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-e3d5b819ccd3459a9325261624b0c313
Source dataset
uspto-grants-2010_11
Patent number
US07838675B2

Reaction notes

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