2,4-Dichlorobenzylamine → HCID 178508416, compound

HRID 1500493Notes

Reaction equation

HRID 1500493 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([OH:8])[C:5]([C:9]([OH:11])=O)=[CH:4][N:3]=1.[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[CH2:20][NH2:21].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[Cl-].[NH4+]>CN(C)C=O.C(N(CC)CC)C>[NH2:1][C:2]1[N:7]=[C:6]([OH:8])[C:5]([C:9]([NH:21][CH2:20][C:14]2[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:13]=2[Cl:12])=[O:11])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 14852,4-Dichlorobenzylamine2×HCID 25517Ammonium ChlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 178508418HCID 178508418, compound

Product 1

HCID 178508416HCID 178508416, compoundYield 51.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a suspension of 2-amino-4-hydroxypyrimidine-5-carboxylic acid (311 mg), (2,4-dichlorophenyl)methanamine (353 mg), and triethylamine (2.8 mL) in N,N-dimethylformamide (8 mL), 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (839 mg) was added at room temperature, and the mixture was stirred for 90 minutes. 2,4-Dichlorobenzylamine (353 mg) and 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (839 mg) were added thereto, and the mixture was stirred for 12 hours. A saturated aqueous ammonium chloride solution was added to the reaction solution, and the mixture was stirred for 1 hour and then filtered. The product collected by filtration was washed with water, dried under reduced pressure, and then suspended in ethyl acetate. This suspension was shaken for 1 hour in an ultrasonic bath and then filtered. The obtained product collected by filtration was dried under reduced pressure to obtain the title compound (326 mg).

Workup

  1. additionwas added at room temperature
  2. stirringthe mixture was stirred for 12 hours
  3. stirringthe mixture was stirred for 1 hour
  4. filtrationfiltered
  5. filtrationThe product collected by filtration
  6. washwas washed with water
  7. customdried under reduced pressure
  8. stirringThis suspension was shaken for 1 hour in an ultrasonic bath
  9. filtrationfiltered
  10. filtrationThe obtained product collected by filtration
  11. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-668d08ee3e8c4c43b3ef1dd99f2eb7ce
Source dataset
uspto-grants-2015_12
Patent number
US09206168B2

Reaction notes

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