Methanesulfonyl chloride → 4-(4-Amino-6-{4-[4-(4-fluoro-3-methyl-phenyl)-1-(2-methanesulfonyloxy-ethyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidin-5-yl)-pyrazole-1-carboxylic acid tert-butyl ester

HRID 2284058Notes

Reaction equation

HRID 2284058 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]=[C:11]([C:13]2[C:14]([NH2:41])=[N:15][CH:16]=[N:17][C:18]=2[N:19]2[CH2:24][CH2:23][CH:22]([C:25]3[N:26]([CH2:38][CH2:39][OH:40])[CH:27]=[C:28]([C:30]4[CH:35]=[CH:34][C:33]([F:36])=[C:32]([CH3:37])[CH:31]=4)[N:29]=3)[CH2:21][CH2:20]2)[CH:10]=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)C(C)C)C.[CH3:51][S:52](Cl)(=[O:54])=[O:53]>C1COCC1>[NH2:41][C:14]1[C:13]([C:11]2[CH:10]=[N:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH:12]=2)=[C:18]([N:19]2[CH2:24][CH2:23][CH:22]([C:25]3[N:26]([CH2:38][CH2:39][O:40][S:52]([CH3:51])(=[O:54])=[O:53])[CH:27]=[C:28]([C:30]4[CH:35]=[CH:34][C:33]([F:36])=[C:32]([CH3:37])[CH:31]=4)[N:29]=3)[CH2:21][CH2:20]2)[N:17]=[CH:16][N:15]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 894427674-(4-amino-6-{4-[4-(4-fluoro-3-methyl-phenyl)-1-(2-hydroxy-ethyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidin-5-yl)-pyrazole-1-carboxylic acid tert-butyl ester

Product 1

HCID 894426624-(4-Amino-6-{4-[4-(4-fluoro-3-methyl-phenyl)-1-(2-methanesulfonyloxy-ethyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidin-5-yl)-pyrazole-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 4-(4-amino-6-{4-[4-(4-fluoro-3-methyl-phenyl)-1-(2-hydroxy-ethyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidin-5-yl)-pyrazole-1-carboxylic acid tert-butyl ester (350.00 mg; 0.62 mmol; 1.00 eq.) in THF 5 ml added ethyl-diisopropyl-amine (0.28 ml; 1.56 mmol; 2.50 eq.), then added drop wised methanesulfonyl chloride (0.10 ml; 1.24 mmol; 2.00 eq.) at 0° C., the reaction mixture was stirred at RT for 1 hr, LC-MS showed desired as major, and starting material disappeared, removed off solvent, directly carried the crude product for next step reaction.

Workup

  1. customremoved off solvent
  2. customfor next step reaction

Sources & evidence

ORD record
ord-5fb19e0d28e144ec90e059b6169ea7bf
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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