Aluminium lithium hydride → 4-[1-(3-Chloro-phenyl)-2-hydroxy-ethyl]-piperazine-1-carboxylic acid (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide

HRID 550839Notes

Reaction equation

HRID 550839 reaction equation
C[O:2][C:3](=O)[CH:4]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=1)[N:5]1[CH2:10][CH2:9][N:8]([C:11](=[O:24])[NH:12][C:13]2[S:14][C:15]3[N:16]=[CH:17][N:18]=[C:19]([O:22][CH3:23])[C:20]=3[N:21]=2)[CH2:7][CH2:6]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:23][O:22][C:19]1[C:20]2[N:21]=[C:13]([NH:12][C:11]([N:8]3[CH2:9][CH2:10][N:5]([CH:4]([C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=4)[CH2:3][OH:2])[CH2:6][CH2:7]3)=[O:24])[S:14][C:15]=2[N:16]=[CH:17][N:18]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 24830454(3-Chloro-phenyl)-[4-(7-methoxy-thiazolo[5,4-d]pyrimidin-2-ylcarbamoyl)-piperazin-1-yl]-acetic acid methyl ester

Product 1

HCID 248304534-[1-(3-Chloro-phenyl)-2-hydroxy-ethyl]-piperazine-1-carboxylic acid (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (3-Chloro-phenyl)-[4-(7-methoxy-thiazolo[5,4-d]pyrimidin-2-ylcarbamoyl)-piperazin-1-yl]-acetic acid methyl ester (100 mg, 0.21 mmol) in tetrahydrofuran (3 mL) at 0° C. was added lithium aluminum hydride (25 mg, 0.66 mmol). The mixture was warmed up to room temperature and stirred for two hours. LCMS analysis indicated a mixture of starting material and product. The reaction was worked up using Feiser's conditions and the crude obtained was then purified using reversed phase HPLC to give 4-[1-(3-Chloro-phenyl)-2-hydroxy-ethyl]-piperazine-1-carboxylic acid (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide as a white powder; LRMS for C19H21ClN6O3S (M+H)+ at m/z=449. The NMR spectrum obtained on the sample is compatible with its structure.

Workup

  1. additiona mixture of starting material and product
  2. customthe crude obtained
  3. customwas then purified

Sources & evidence

ORD record
ord-9f6c5dd620f1477ab5a11017b37a6645
Source dataset
uspto-grants-2011_05
Patent number
US07947692B2

Reaction notes

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