Methyl bromoacetate → (3-{4-Chloro-3-[(1-hydroxy-cycloheptylmethyl)-carbamoyl]-phenyl}-5-methyl-pyrazol-1-yl)-acetic acid methyl ester

HRID 1988378Notes

Reaction equation

HRID 1988378 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([C:20]2[CH:24]=[C:23]([CH3:25])[NH:22][N:21]=2)=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][C:8]1([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:5].[CH3:26][O:27][C:28](=[O:31])[CH2:29]Br>CN(C)C=O>[CH3:26][O:27][C:28](=[O:31])[CH2:29][N:22]1[C:23]([CH3:25])=[CH:24][C:20]([C:17]2[CH:18]=[CH:19][C:2]([Cl:1])=[C:3]([C:4](=[O:5])[NH:6][CH2:7][C:8]3([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)[CH:16]=2)=[N:21]1

Participants

4

Reactant 2

HCID 60984Methyl bromoacetateHCID 111875812-chloro-N-(1-hydroxy-cycloheptylmethyl)-5-(5-methyl-1H-pyrazol-3-yl)-benzamide

Product 1

HCID 58818174(3-{4-Chloro-3-[(1-hydroxy-cycloheptylmethyl)-carbamoyl]-phenyl}-5-methyl-pyrazol-1-yl)-acetic acid methyl esterYield 80.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-chloro-N-(1-hydroxy-cycloheptylmethyl)-5-(5-methyl-1H-pyrazol-3-yl)-benzamide (1.08 g, 3 mmol), 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,2,3-diazaphosphorine on polystyrene (2.0 g, 4.6 mmol) and bromo-acetic acid methyl ester (0.69 g, 4.5 mmol) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 2 h. The mixture was filtered and washed with dichloromethane. The filtrate was concentrated in vacuo. The residue was triturated with ethyl acetate to afford the title compound (1.05 g). (3-{4-Chloro-3-[(1-hydroxy-cycloheptylmethyl)-carbamoyl]-phenyl}-5-methyl-pyrazol-1-yl)-acetic acid.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with dichloromethane
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-7cc3b85c7a044caa8d4434e1ab0a1324
Source dataset
uspto-grants-2009_06
Patent number
US07553972B2

Reaction notes

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