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

HRID 1959010Notes

Reaction equation

HRID 1959010 reaction equation
[F:1][C:2]1[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:3]=1[CH2:4][S:5][C:6]1[N:11]=[C:10]([O:12][C@H:13]([CH3:19])[C:14](OCC)=[O:15])[CH:9]=[C:8]([NH:20][S:21]([N:24]2[CH2:29][CH2:28][N:27]([CH2:30][CH3:31])[CH2:26][CH2:25]2)(=[O:23])=[O:22])[N:7]=1.[Li+].[BH4-].[NH4+].[Cl-]>C1COCC1>[F:1][C:2]1[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:3]=1[CH2:4][S:5][C:6]1[N:7]=[C:8]([NH:20][S:21]([N:24]2[CH2:25][CH2:26][N:27]([CH2:30][CH3:31])[CH2:28][CH2:29]2)(=[O:22])=[O:23])[CH:9]=[C:10]([O:12][C@H:13]([CH3:19])[CH2:14][OH:15])[N:11]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 53628378Ethyl (2R)-2-[(2-[(2,3-difluorobenzyl)thio]-6-{[(4-ethylpiperazin-1-yl)sulfonyl]amino}pyrimidin-4-yl)oxy]propanoate

Product 1

HCID 59558846N-[2-[[(2,3-Difluorophenyl)methyl]thio]-6-[(1R)-2-hydroxy-1-methylethoxy]-4-pyrimidinyl]-4-ethyl-piperazine-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl(2R)-2-[(2-[(2,3-Difluorobenzyl)thio]-6-{[(4-ethylpiperazin-1-yl)sulfonyl]amino}pyrimidin-4-yl)oxy]propanoate (the product from step i) (0.72 g) in THF (10 ml) was added 2M LiBH4 in TI-IF (1.3 ml). The reaction was then stirred for 18 h at RT. Saturated NH4Cl (150 ml) was then added to the reaction mixture which was extracted with DCM (3×150 ml). Organics were combined, dried (MgSO4) and reduced in vacuo and the resulting residue was purified by prep HPLC to give the title compound as a white solid.

Workup

  1. extractionwas extracted with DCM (3×150 ml)
  2. dry with materialdried (MgSO4)
  3. customthe resulting residue was purified by prep HPLC

Sources & evidence

ORD record
ord-fe8544a9d6e74e6685c24260833ba5cb
Source dataset
uspto-grants-2013_04
Patent number
US08410123B2

Reaction notes

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