Lithium borohydride → N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(1R)-2-hydroxy-1-methylethoxy]-4-pyrimidinyl]-1-pyrrolidinesulfonamide

HRID 1958934Notes

Reaction equation

HRID 1958934 reaction equation
[CH2:1]([O:3][C:4](=O)[C@H:5]([O:7][C:8]1[CH:13]=[C:12]([NH:14][S:15]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)(=[O:17])=[O:16])[N:11]=[C:10]([S:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:26]=2[F:32])[N:9]=1)[CH3:6])[CH3:2].[BH4-].[Li+]>C1COCC1>[CH3:2][CH2:1][O:3][CH2:4][CH3:5].[CH3:28][CH2:27][CH2:26][CH:25]([CH3:30])[CH3:24].[F:32][C:26]1[C:27]([F:31])=[CH:28][CH:29]=[CH:30][C:25]=1[CH2:24][S:23][C:10]1[N:11]=[C:12]([NH:14][S:15]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)(=[O:16])=[O:17])[CH:13]=[C:8]([O:7][C@H:5]([CH3:6])[CH2:4][OH:3])[N:9]=1

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 536283522-[[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(1-pyrrolidinylsulfonyl)amino]-4-pyrimidinyl]oxy]-(2R)-propanoic acid ethyl ester

Product 2

HCID 11597794N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(1R)-2-hydroxy-1-methylethoxy]-4-pyrimidinyl]-1-pyrrolidinesulfonamideHCID 21882825Ether isohexane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The title compound was prepared according to the procedure outlined in example 24 using a mixture of 2-[[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(1-pyrrolidinylsulfonyl)amino]-4-pyrimidinyl]oxy]-(2R)-propanoic acid ethyl ester, (the product of step i) (0.38 g), THF (8 mL) and 2M lithium borohydride in THF (1.3 mL). Purification was by reverse phase HPLC (symmetry as the stationary phase and TFA/acetonitrile as the mobile phase). The resulting oil was titurated with methanol, toluene, DCM, then ether/iso-hexane to give the title compound as a white solid. Yield: 0.15 g

Workup

  1. customThe title compound was prepared
  2. customPurification

Sources & evidence

ORD record
ord-5dccf67da8884b09a80dc2eeacb12c74
Source dataset
uspto-grants-2013_04
Patent number
US08410123B2

Reaction notes

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