Trifluoroacetic acid methylene chloride → N-{2-[(2,3-Difluorobenzyl)thio]-6-methoxypyrimidin-4-yl}-4-glycylpiperazine-1-sulfonamide, hydrochloride salt

HRID 1959072Notes

Reaction equation

HRID 1959072 reaction equation
[F:1][C:2]1[C:38]([F:39])=[CH:37][CH:36]=[CH:35][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]([C:22](=[O:32])[CH2:23][NH:24]C(=O)OC(C)(C)C)[CH2:18][CH2:17]2)(=[O:15])=[O:14])[CH:9]=[C:8]([O:33][CH3:34])[N:7]=1.C(O)(C(F)(F)F)=O.C(Cl)[Cl:48]>>[ClH:48].[F:1][C:2]1[C:38]([F:39])=[CH:37][CH:36]=[CH:35][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]([C:22](=[O:32])[CH2:23][NH2:24])[CH2:20][CH2:21]2)(=[O:14])=[O:15])[CH:9]=[C:8]([O:33][CH3:34])[N:7]=1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 86619892tert-Butyl (2-{4-[({2-[(2,3-difluorobenzyl)thio]-6-methoxypyrimidin-4-yl}amino)sulfonyl]piperazin-1-yl}-2-oxoethyl)carbamate

Product 1

HCID 131728547N-{2-[(2,3-Difluorobenzyl)thio]-6-methoxypyrimidin-4-yl}-4-glycylpiperazine-1-sulfonamide, hydrochloride salt

Procedure

A solution of tert-butyl (2-{4-[({2-[(2,3-difluorobenzyl)thio]-6-methoxypyrimidin-4-yl}amino)sulfonyl]piperazin-1-yl}-2-oxoethyl)carbamate (the product of step ii, 0.19 g) in 10% TFA/DCM (5 mL) was stirred at room temperature for 3 h. The solution was evaporated, and then redissolved in 4N HCl in dioxane (2 mL) and MeOH (8 mL). Evaporation gave a crude residue that was triturated in Et2O, filtered and dried in a vacuum oven at 40° C. overnight to give the title compound as a white solid. Yield: 140 mg.

Workup

  1. customThe solution was evaporated
  2. dissolutionredissolved in 4N HCl in dioxane (2 mL)
  3. customEvaporation
  4. customgave a crude residue that
  5. customwas triturated in Et2O
  6. filtrationfiltered
  7. customdried in a vacuum oven at 40° C. overnight

Sources & evidence

ORD record
ord-0e58190e7b4445f990870ec64f12a0c3
Source dataset
uspto-grants-2013_04
Patent number
US08410123B2

Reaction notes

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