tert-butyl 4-{[(2-[(2,3-difluorobenzyl)thio]-6-{(1R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethoxy}pyrimidin-4-yl)amino]sulfonyl}piperazine-1-carboxylate → N-[2-[[(2,3-Difluorophenyl)methyl]thio]-6-[[(1R,2S)-2,3-dihydroxy-1-methylpropyl]oxy}-4-pyrimidinyl]-1-piperazinesulfonamide

HRID 1024912Notes

Reaction equation

HRID 1024912 reaction equation
[F:1][C:2]1[C:42]([F:43])=[CH:41][CH:40]=[CH:39][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(OC(C)(C)C)=O)[CH2:18][CH2:17]2)(=[O:15])=[O:14])[CH:9]=[C:8]([O:29][C@@H:30]([C@@H:32]2[CH2:36][O:35]C(C)(C)[O:33]2)[CH3:31])[N:7]=1>FC(F)(F)C(O)=O.C(Cl)Cl>[F:1][C:2]1[C:42]([F:43])=[CH:41][CH:40]=[CH:39][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][NH:19][CH2:20][CH2:21]2)(=[O:15])=[O:14])[CH:9]=[C:8]([O:29][C@H:30]([CH3:31])[C@@H:32]([OH:33])[CH2:36][OH:35])[N:7]=1

Participants

3

Reactant 1

HCID 53628363tert-butyl 4-{[(2-[(2,3-difluorobenzyl)thio]-6-{(1R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethoxy}pyrimidin-4-yl)amino]sulfonyl}piperazine-1-carboxylate

Product 1

HCID 59558751N-[2-[[(2,3-Difluorophenyl)methyl]thio]-6-[[(1R,2S)-2,3-dihydroxy-1-methylpropyl]oxy}-4-pyrimidinyl]-1-piperazinesulfonamide

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of tert-butyl 4-{[(2-[(2,3-difluorobenzyl)thio]-6-((1R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethoxy}pyrimidin-4-yl)amino]sulfonyl)piperazine-1-carboxylate (the product of step i) (0.23 g) in 10% trifluoroacetic acid/DCM (5 mL) was stirred at room temperature for 1 h. The mixture was evaporated to dryness in vacuo. The resulting crude oil was purified by reverse phase HPLC (75% to 5% gradient of 0.1% aqueous ammonium acetate in acetonitrile as eluent) to give the title compound as a white solid, Yield: 40 mg.

Workup

  1. customThe mixture was evaporated to dryness in vacuo
  2. customThe resulting crude oil was purified by reverse phase HPLC (75% to 5% gradient of 0.1% aqueous ammonium acetate in acetonitrile as eluent)

Sources & evidence

ORD record
ord-5a8ff0e060b342cea0ee8a29a167c704
Source dataset
uspto-grants-2014_05
Patent number
US08722883B2

Reaction notes

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