1-Piperazinecarboxylic acid, 4-(4-aMinophenyl)-, phenylMethyl ester → HCID 86712628, compound

HRID 1778959Notes

Reaction equation

HRID 1778959 reaction equation
CS([C:5]1[N:10]=[C:9]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH:8]=[CH:7][N:6]=1)(=O)=O.[NH2:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]2[CH2:36][CH2:35][N:34]([C:37]([O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[O:38])[CH2:33][CH2:32]2)=[CH:27][CH:26]=1>C(O)(C(F)(F)F)=O>[CH3:23][O:22][C:20](=[O:21])[CH2:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH2:12][CH2:11][C:9]1[CH:8]=[CH:7][N:6]=[C:5]([NH:24][C:25]2[CH:26]=[CH:27][C:28]([N:31]3[CH2:32][CH2:33][N:34]([C:37]([O:39][CH2:40][C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=4)=[O:38])[CH2:35][CH2:36]3)=[CH:29][CH:30]=2)[N:10]=1

Participants

4

Reactant 2

HCID 574896191-Piperazinecarboxylic acid, 4-(4-aMinophenyl)-, phenylMethyl esterHCID 86712629HCID 86712629, compound

Product 1

HCID 86712628HCID 86712628, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent3×

Conditions

Temperature
100 °C

Procedure

A solution of methyl 2-(2-(2-(2-(methylsulfonyl)pyrimidin-4-yl)ethyl)phenyl)acetate (A3) (150 mg, 449 μmol) and benzyl 4-(4-aminophenyl)piperazine-1-carboxylate (K2) (168 mg, 538 μmol) in TFE (5 mL) containing TFA (180 μL) was heated at 100° C. under microwave irradiation for 60 minutes. Additional TFA (200 μL) was added and the resulting solution heated at 120° C. under microwave irradiation for a further 40 minutes. Additional TFA (200 μL) was again added and the mixture was heated at 150° C. under microwave irradiation for a further 20 minutes. The resulting mixture was adsorbed onto silica gel and purified by column chromatography (Biotage Isolera, SiO2 cartridge, 0-100% EtOAc in petroleum benzine 40-60° C.) to give the title compound A4 as a brown oil (76 mg, 30%). LCMS-A: rt 6.212 min; m/z 566.2 [M+H]+.

Workup

  1. temperaturethe resulting solution heated at 120° C. under microwave irradiation for a further 40 minutes
  2. temperaturethe mixture was heated at 150° C. under microwave irradiation for a further 20 minutes
  3. custompurified by column chromatography (Biotage Isolera, SiO2 cartridge, 0-100% EtOAc in petroleum benzine 40-60° C.)

Sources & evidence

ORD record
ord-67d6fc55d282403d9aa58d499b0e0c54
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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