3,5-Dichlorobenzoic acid → HCID 68679610, compound

HRID 1444593Notes

Reaction equation

HRID 1444593 reaction equation
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([Cl:17])[CH:16]=1)[C:11]([OH:13])=O.[C:18]([O:22][C:23]([N:25]1[CH2:35][CH2:34][C:28]2[N:29]=[C:30]([NH2:33])[N:31]=[CH:32][C:27]=2[CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].[OH-].[Na+]>CN(C=O)C.C(Cl)Cl>[C:18]([O:22][C:23]([N:25]1[CH2:35][CH2:34][C:28]2[N:29]=[C:30]([NH:33][C:11](=[O:13])[C:10]3[CH:14]=[C:15]([Cl:17])[CH:16]=[C:8]([Cl:7])[CH:9]=3)[N:31]=[CH:32][C:27]=2[CH2:26]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

7

Reactant 4

HCID 58113,5-Dichlorobenzoic acidHCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 29184118tert-butyl 2-amino-5H,6H,7H,8H-pyrido[4,3-d]pyrimidine-6-carboxylate

Product 1

HCID 68679610HCID 68679610, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride 1184 μl (13.8 mmol) and two drops of DMF were added to a solution of 3,5-dichlorobenzoic acid 527 mg (2.76 mmol) in CH2Cl2 and stirring was performed for 1 h at RT under nitrogen as inert gas. After removal of the solvent, the 3,5-dichlorobenzoyl chloride was dissolved in pyridine (30 ml). 2-Amino-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylic acid tert-butyl ester 599 mg (2.39 mmol) was added to this solution at 0° C. and stirring was performed for 2 h at 0° C. and then for 2 h at RT under nitrogen as inert gas. After the addition of aqueous 1 M NaOH (40 ml) and stirring for 20 minutes, CH2Cl2 (50 ml) was added and the aqueous phase extracted with CH2Cl2 (3×20 ml). The combined organic phases were dried over Na2SO4. After filtration and removal of the solvent, purification was performed by means of column chromatography and the product 2-(3,5-dichloro-benzoylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylic acid tert-butyl ester 573 mg (1.35 mmol, 57% of theoretical) was obtained.

Workup

  1. customAfter removal of the solvent
  2. dissolutionthe 3,5-dichlorobenzoyl chloride was dissolved in pyridine (30 ml)
  3. stirringstirring
  4. waitwas performed for 2 h at 0° C.
  5. waitfor 2 h at RT under nitrogen as inert gas
  6. stirringstirring for 20 minutes
  7. extractionthe aqueous phase extracted with CH2Cl2 (3×20 ml)
  8. dry with materialThe combined organic phases were dried over Na2SO4
  9. filtrationAfter filtration and removal of the solvent, purification

Sources & evidence

ORD record
ord-563121c134954f33a0e9569e292d9133
Source dataset
uspto-grants-2010_02
Patent number
US07662828B2

Reaction notes

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