Ammonium formate → 2-(2-((2S)-4-((5-amino-2-thiophenyl)sulfonyl)-2-methyl-1-piperazinyl)-5-pyrimidinyl)-1,1,1-trifluoro-2-propanol

HRID 1972506Notes

Reaction equation

HRID 1972506 reaction equation
[N+:1]([C:4]1[S:8][C:7]([S:9]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[N:23]=[CH:22][C:21]([C:24]([OH:30])([CH3:29])[C:25]([F:28])([F:27])[F:26])=[CH:20][N:19]=3)[C@@H:14]([CH3:31])[CH2:13]2)(=[O:11])=[O:10])=[CH:6][CH:5]=1)([O-])=O.C([O-])=O.[NH4+]>CCO.C(Cl)Cl.[Pd]>[NH2:1][C:4]1[S:8][C:7]([S:9]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[N:23]=[CH:22][C:21]([C:24]([OH:30])([CH3:29])[C:25]([F:27])([F:28])[F:26])=[CH:20][N:19]=3)[C@@H:14]([CH3:31])[CH2:13]2)(=[O:10])=[O:11])=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 569325732-(2-((2S)-4-((5-nitro-2-thiophenyl)sulfonyl)-2-methyl-1-piperazinyl)-5-pyrimidinyl)-1,1,1-trifluoro-2-propanol

Product 1

HCID 665823372-(2-((2S)-4-((5-amino-2-thiophenyl)sulfonyl)-2-methyl-1-piperazinyl)-5-pyrimidinyl)-1,1,1-trifluoro-2-propanolYield 22.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

In a 50-mL round bottomed flask, a mixture of 2-(2-((2S)-4-((5-nitro-2-thiophenyl)sulfonyl)-2-methyl-1-piperazinyl)-5-pyrimidinyl)-1,1,1-trifluoro-2-propanol (108 mg, 0.224 mmol), ammonium formate (30.1 mg, 0.478 mmol, Sigma-Aldrich, St. Louis, Mo.), and 10% Pd/C (25.4 mg, 0.024 mmol) in EtOH (10 mL) was stirred under an atmosphere of H2 (1 atm) for 18 h. Afterwards, the mixture was filtered through a plug of Celite and the filtrate was concentrated to give the crude product. The crude product was dissolved in CH2Cl2 and filtered through a plug of silica gel. The filtrate was concentrated to give 2-(2-((2S)-4-((5-amino-2-thiophenyl)sulfonyl)-2-methyl-1-piperazinyl)-5-pyrimidinyl)-1,1,1-trifluoro-2-propanol (23 mg) as a mixture of two isomers.

Workup

  1. filtrationAfterwards, the mixture was filtered through a plug of Celite
  2. concentrationthe filtrate was concentrated
  3. customto give the crude product
  4. filtrationfiltered through a plug of silica gel
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-36559de930d34f63906b8510d0da47ed
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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