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

HRID 1024871Notes

Reaction equation

HRID 1024871 reaction equation
[N:1]1([S:5]([NH:8][C:9]2[N:14]=[C:13]([S:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=3[F:24])[N:12]=[C:11]([O:25][C@@H:26]([CH3:32])[C:27](OCC)=[O:28])[CH:10]=2)(=[O:7])=[O:6])[CH2:4][CH2:3][CH2:2]1.[BH4-].[Li+]>C1COCC1>[F:24][C:18]1[C:19]([F:23])=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][S:15][C:13]1[N:14]=[C:9]([NH:8][S:5]([N:1]2[CH2:4][CH2:3][CH2:2]2)(=[O:6])=[O:7])[CH:10]=[C:11]([O:25][C@@H:26]([CH3:32])[CH2:27][OH:28])[N:12]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 670512112-[[6-[(1-azetidinylsulfonyl)amino]-2-[[(2,3-difluorophenyl)methyl]thio]-4-pyrimidinyl]oxy]-(2S)-propanoic acid ethyl ester

Product 1

HCID 59558803N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(1S)-2-hydroxy-1-methylethoxy]-4-pyrimidinyl]-1-azetidinesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The title compound was prepared according to the procedure outlined in example 24 using 2-[[6-[(1-azetidinylsulfonyl)amino]-2-[[(2,3-difluorophenyl)methyl]thio]-4-pyrimidinyl]oxy]-(2S)-propanoic acid, ethyl ester, (the product of step ii) (0.28 g), THF (8 mL) and 2M lithium borohydride in THF (0.57 mL). Purification was by column chromatography on silica using EtOAc/isohexane (2:3) as eluent 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-216dd8400cab4fe5b4d08eff16762064
Source dataset
uspto-grants-2014_05
Patent number
US08722883B2

Reaction notes

Loading…