Lithium borohydride → 2{4-[4-Chloro-2-(5-chloro-pyridin-2-ylcarbamoyl)-phenylcarbamoyl]-phenyl}-2-methyl-propyl alcohol

HRID 971166Notes

Reaction equation

HRID 971166 reaction equation
C[O:2][C:3](=O)[C:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:32])[NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[C:22](=[O:31])[NH:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][N:25]=2)=[CH:9][CH:8]=1)([CH3:6])[CH3:5].[Li+].[BH4-]>C1COCC1>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:13]([C:10]2[CH:11]=[CH:12][C:7]([C:4]([CH3:6])([CH3:5])[CH2:3][OH:2])=[CH:8][CH:9]=2)=[O:32])=[C:16]([C:22](=[O:31])[NH:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][N:25]=2)[CH:17]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 590197632{4-[4-Chloro-2-(5-chloro-pyridin-2-ylcarbamoyl)-phenylcarbamoyl]-phenyl}-2-methyl-propionic acid methyl ester

Product 1

HCID 590201982{4-[4-Chloro-2-(5-chloro-pyridin-2-ylcarbamoyl)-phenylcarbamoyl]-phenyl}-2-methyl-propyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2{4-[4-Chloro-2-(5-chloro-pyridin-2-ylcarbamoyl)-phenylcarbamoyl]-phenyl}-2-methyl-propionic acid methyl ester (485.0 mg, 1 mmol) in THF was added LiBH4 (2.0 ml, 2.0 M solution in THF). The mixture was stirred at 60° C. over night. The reaction mixture was cooled, and quenched with sat'd NH4Cl. HPLC purification gave 2{4-[4-Chloro-2-(5-chloro-pyridin-2-ylcarbamoyl)-phenylcarbamoyl]-phenyl}-2-methyl-propyl alcohol as white solid. MS found: (M+1)+=457.9.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customquenched with sat'd NH4Cl
  3. customHPLC purification

Sources & evidence

ORD record
ord-09c4d4f1075742718c3f3d45e1be8bcd
Source dataset
uspto-grants-2007_12
Patent number
US07312214B2

Reaction notes

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