Lithium borohydride → HCID 86691764, compound

HRID 1024980Notes

Reaction equation

HRID 1024980 reaction equation
C([O:3][C:4](=O)[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([S:12](=[O:35])(=[O:34])[NH:13][C:14]2[CH:19]=[C:18]([O:20][CH3:21])[N:17]=[C:16]([S:22]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:27]=3[F:33])(=[O:24])=[O:23])[N:15]=2)[CH2:8][CH2:7]1)C.[BH4-].[Li+]>C1COCC1>[F:33][C:27]1[C:28]([F:32])=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][S:22]([C:16]1[N:15]=[C:14]([NH:13][S:12]([N:9]2[CH2:8][CH2:7][N:6]([CH2:5][CH2:4][OH:3])[CH2:11][CH2:10]2)(=[O:35])=[O:34])[CH:19]=[C:18]([O:20][CH3:21])[N:17]=1)(=[O:23])=[O:24]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 86691763HCID 86691763, compound2×

Product 1

HCID 86691764HCID 86691764, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared according to the procedure outlined in example 24 using a mixture of {4-[2-(2,3-Difluoro-benzylsulfonyl)-6-methoxy-pyrimidin-4-ylsulfamoyl]-piperazin-1-yl}-acetic acid ethyl ester (the product from example 86 step i) (031 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. Yield: 13 mg

Workup

  1. customThe title compound was prepared
  2. customPurification

Sources & evidence

ORD record
ord-5f7857f894aa4ce1b0b004e0462fa61b
Source dataset
uspto-grants-2014_05
Patent number
US08722883B2

Reaction notes

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