Cesium carbonate → 4'-Chloro-2-[4-(3-cyano-7-cyclohexyl-pyrazolo[1,5-a]pyrimidin-6-yl)-phenoxymethyl]-biphenyl-4-carboxylic acid methyl ester

HRID 270963Notes

Reaction equation

HRID 270963 reaction equation
[CH:1]1([C:7]2[N:12]3[N:13]=[CH:14][C:15]([C:16]#[N:17])=[C:11]3[N:10]=[CH:9][C:8]=2[C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:25][O:26][C:27]([C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)=[C:31]([CH2:42]Br)[CH:30]=1)=[O:28].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:25][O:26][C:27]([C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)=[C:31]([CH2:42][O:24][C:21]2[CH:20]=[CH:19][C:18]([C:8]3[CH:9]=[N:10][C:11]4[N:12]([N:13]=[CH:14][C:15]=4[C:16]#[N:17])[C:7]=3[CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[CH:23][CH:22]=2)[CH:30]=1)=[O:28]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 159580147-Cyclohexyl-6-(4-hydroxyphenyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrileHCID 691546302-Bromomethyl-4'-chloro-biphenyl-4-carboxylic acid methyl ester

Product 1

HCID 691547374'-Chloro-2-[4-(3-cyano-7-cyclohexyl-pyrazolo[1,5-a]pyrimidin-6-yl)-phenoxymethyl]-biphenyl-4-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Alkylation of 7-cyclohexyl-6-(4-hydroxy-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carbonitrile with 2-bromomethyl-4′-chloro-biphenyl-4-carboxylic acid methyl ester was carried out in dimethylformamide (DMF) using cesium carbonate and following a previously described experimental procedure to give 4′-chloro-2-[4-(3-cyano-7-cyclohexyl-pyrazolo[1,5-a]pyrimidin-6-yl)-phenoxymethyl]-biphenyl-4-carboxylic acid methyl ester. This compound was converted to its corresponding tetrazole 4′-chloro-2-{4-[7-cyclohexyl-3-(1H-tetrazol-5-yl)-pyrazolo[1,5-a]pyrimidin-6-yl]-phenoxymethyl}-biphenyl-4-carboxylic acid methyl ester (475) via a previously described procedure. Finally, 4′-chloro-2-{4-[7-cyclohexyl-3-(1H-tetrazol-5-yl)-pyrazolo[1,5-a]pyrimidin-6-yl]-phenoxymethyl}-biphenyl-4-carboxylic acid (490) was obtained following a standard LiOH saponification protocol.

Sources & evidence

ORD record
ord-f20f90ce787d46d1a8f1cb8b58d0e3db
Source dataset
uspto-grants-2008_11
Patent number
US07449488B2

Reaction notes

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