Cyclopropylamine → HCID 83103480, compound

HRID 2386242Notes

Reaction equation

HRID 2386242 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH:11]1[C:16]([OH:18])=O.CC[N:21]([CH:25]([CH3:27])[CH3:26])C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1(N)CC1>O.CS(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH:11]2[C:16]([NH:21][CH:25]2[CH2:27][CH2:26]2)=[O:18])[C:5]([F:9])=[CH:4][N:3]=1

Participants

8

Reactant 5

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 33401523-Morpholinecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 83103480HCID 83103480, compoundYield 21.62%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A round-bottomed flask equipped with a magnetic stirrer was added 2,4-dichloro-5-fluoropyrimidine (0.835 g, 5 mmol), DMSO (1 ml), morpholine-3-carboxylic acid (0.656 g, 5.00 mmol) and DIPEA (3.49 ml, 20.00 mmol). The reaction was stirred at 80° C. for 10 minutes then cooled to ambient temperature, HATU (2.85 g, 7.50 mmol) was added followed by cyclopropanamine (0.526 ml, 7.50 mmol) and the reaction mixture was again heated at 80° C. for 2 hours. Upon completion the reaction was suspended in water and filtered. The collected solid was washed successively with water, small amount of ethanol and diethyl ether. The solid was dried in vacuo for 16 hours to afford 4-(2-chloro-5-fluoropyrimidin-4-yl)-N-cyclopropylmorpholine-3-carboxamide (0.325 g, 1.081 mmol, 21.62% yield) as a white solid.

Workup

  1. customA round-bottomed flask equipped with a magnetic stirrer
  2. temperaturethen cooled to ambient temperature
  3. temperaturethe reaction mixture was again heated at 80° C. for 2 hours
  4. filtrationfiltered
  5. washThe collected solid was washed successively with water, small amount of ethanol and diethyl ether
  6. customThe solid was dried in vacuo for 16 hours

Sources & evidence

ORD record
ord-b5879e2ec22b49298a7ac7ae31922599
Source dataset
uspto-grants-2012_09
Patent number
US08268819B2

Reaction notes

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