Water → HCID 178473464, compound

HRID 1167540Notes

Reaction equation

HRID 1167540 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH2:19])[N:14]=3)=[CH:11][NH:10][N:9]=2)=[CH:4][CH:3]=1.C1C=NC(NS(C2C=CC(N)=CC=2)(=O)=O)=NC=1.Cl[C:38]([O:40][CH2:41][CH3:42])=[O:39].O>N1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:38](=[O:39])[O:40][CH2:41][CH3:42])[N:14]=3)=[CH:11][NH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5215SulfadiazineHCID 10928Ethyl chloroformateHCID 1785083854-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]-2-pyrimidinamine

Product 1

HCID 178473464HCID 178473464, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a suspension of 4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]-2-pyrimidinamine prepared in accordance with Example A-306 (0.26 g, 0.001 mol) in 5 mL of pyridine was added ethyl chloroformate dropwise. After the addition, the clear solution was stirred at room temperature for 6 hours. Water was added and the aqueous phase was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated and the crude was trituated with ether to give 0.15 g of product, ethyl [4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]-2-pyrimidinyl]carbamate, as a white solid (46% yield), mp: 163-165° C.; Anal. Calc'd for C16H14FN5O2: C, 58.71; H, 4.31; N, 21.04. Found: C, 59.22; H, 4.51; N, 21.66.

Workup

  1. additionAfter the addition
  2. extractionthe aqueous phase was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-0f1ccf4c6c0d40a891ea34fbee722b87
Source dataset
uspto-grants-2003_09
Patent number
US06617324B1

Reaction notes

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