Lithium borohydride → 4-(2-Hydroxy-ethyl)-piperazine-1-sulfonic acid [2-(2,3-difluoro-benzylsulfanyl)-6-methoxy-pyrimidin-4-yl]-amide

HRID 1959040Notes

Reaction equation

HRID 1959040 reaction equation
C([O:3][C:4](=O)[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([S:12](=[O:33])(=[O:32])[NH:13][C:14]2[CH:19]=[C:18]([O:20][CH3:21])[N:17]=[C:16]([S:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:25]=3[F:31])[N:15]=2)[CH2:8][CH2:7]1)C.[BH4-].[Li+]>C1COCC1>[F:31][C:25]1[C:26]([F:30])=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][S:22][C:16]1[N:15]=[C:14]([NH:13][S:12]([N:9]2[CH2:10][CH2:11][N:6]([CH2:5][CH2:4][OH:3])[CH2:7][CH2:8]2)(=[O:33])=[O:32])[CH:19]=[C:18]([O:20][CH3:21])[N:17]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 53628396{4-[2-(2,3-Difluoro-benzylsulfanyl)-6-methoxy-pyrimidin-4-ylsulfamoyl]-piperazin-1-yl}-acetic acid ethyl ester2×

Product 1

HCID 595588024-(2-Hydroxy-ethyl)-piperazine-1-sulfonic acid [2-(2,3-difluoro-benzylsulfanyl)-6-methoxy-pyrimidin-4-yl]-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The title compound was prepared according to the procedure outlined in example 24 using a mixture of {4-[2-(2,3-Difluoro-benzylsulfanyl)-6-methoxy-pyrimidin-4-ylsulfamoyl]-piperazin-1-yl}-acetic acid ethyl ester (the product from example 86 step i) (0.31 g) lithium borohydride (1M solution in THF (1.2 mL) in THF (5 mL). Purification was by reverse phase HPLC (symmetry as the stationary phase and NH4OAc/acetonitrile as the mobile phase) then titurated with Toluene, MeOH followed by DCM to give the title compound as a white solid.

Workup

  1. customThe title compound was prepared
  2. customPurification

Sources & evidence

ORD record
ord-5353f7f5f1334cfd92a578e74c52ed38
Source dataset
uspto-grants-2013_04
Patent number
US08410123B2

Reaction notes

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