4-Nitrophenyl chloroformate → 4-Nitrophenyl 4-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carboxylate

HRID 1478286Notes

Reaction equation

HRID 1478286 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([N:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)=[N:7][C:6]=12.[C:17](Cl)(=[O:28])[O:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1>CCOC(C)=O>[N+:25]([C:22]1[CH:21]=[CH:20][C:19]([O:18][C:17]([N:14]2[CH2:15][CH2:16][N:11]([C:8]3[CH:9]=[CH:10][N:5]4[N:4]=[CH:3][C:2]([Br:1])=[C:6]4[N:7]=3)[CH2:12][CH2:13]2)=[O:28])=[CH:24][CH:23]=1)([O-:27])=[O:26]

Participants

4

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 866974343-Bromo-5-(piperazin-1-yl)pyrazolo[1,5-a]pyrimidine

Product 1

HCID 866974514-Nitrophenyl 4-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To 2.00 g (7.09 mmol) of 3-bromo-5-piperazin-1-yl-pyrazolo[1,5-a]pyrimidine dissolved in 40 mL of EtOAc at 0° C., was added 1.71 g (8.51 mmol) of 4-nitrophenyl carbonochloridate, followed by 1.97 mL (14.18 mmol) of TEA. After 5 minutes stirring at 0° C., the ice bath was removed, and stirring continued at RT for about 2 hr. It was diluted with 50 mL of 50% EtOAc/hex. The desired product was filtered out, and dried to obtain 3.17 g (100% yield) of an off-white solid.

Workup

  1. customthe ice bath was removed
  2. stirringstirring
  3. waitcontinued at RT for about 2 hr
  4. additionIt was diluted with 50 mL of 50% EtOAc/hex
  5. filtrationThe desired product was filtered out
  6. customdried

Sources & evidence

ORD record
ord-32303684343a4b9495218c52c2f24156
Source dataset
uspto-grants-2016_08
Patent number
US09403832B2

Reaction notes

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