Trifluoroacetic acid → N-[6-(3-bromo-benzenesulfonyl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl]-3-chloro-benzamide

HRID 1444602Notes

Reaction equation

HRID 1444602 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:34][CH2:33][C:18]2[N:19]=[C:20]([NH:23][C:24](=[O:32])[C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=3)[N:21]=[CH:22][C:17]=2[CH2:16]1)=O)(C)(C)C.C(N(CC)CC)C.[Br:42][C:43]1[CH:44]=[C:45]([S:49](Cl)(=[O:51])=[O:50])[CH:46]=[CH:47][CH:48]=1>C(Cl)Cl>[Br:42][C:43]1[CH:44]=[C:45]([S:49]([N:15]2[CH2:34][CH2:33][C:18]3[N:19]=[C:20]([NH:23][C:24](=[O:32])[C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=4)[N:21]=[CH:22][C:17]=3[CH2:16]2)(=[O:51])=[O:50])[CH:46]=[CH:47][CH:48]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 17943m-Bromobenzenesulphonyl chlorideHCID 686786472-(3-chloro-benzoylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylic acid tert-butyl ester

Product 1

HCID 11684864N-[6-(3-bromo-benzenesulfonyl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl]-3-chloro-benzamideYield 82.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Trifluoroacetic acid 6.2 ml (81 mmol) was added to a solution of 2-(3-chloro-benzoylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylic acid tert-butyl ester 487 mg (1.25 mmol) in CH2Cl2 (8 ml) under nitrogen as inert gas and stirring was performed for 1.5 h at RT. After removal of the solvent, the intermediate (3-chloro-N-(5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl)-benzamide trifluoroacetate) was dissolved in CH2Cl2 (15 ml). After the addition of triethylamine 820 μl (5.84 mmol), the solution was cooled to 0° C. and 3-bromo benzenesulfonyl chloride 311 mg (1.37 mmol) was added. The reaction mixture was stirred for 1 h at 0° C. and then overnight at RT. After removal of the solvent, purification was performed by means of column chromatography and the product N-[6-(3-bromo-benzenesulfonyl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl]-3-chloro-benzamide 525 mg (81% of theoretical) was obtained.

Workup

  1. customAfter removal of the solvent
  2. dissolutionthe intermediate (3-chloro-N-(5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl)-benzamide trifluoroacetate) was dissolved in CH2Cl2 (15 ml)
  3. stirringThe reaction mixture was stirred for 1 h at 0° C.
  4. customovernight
  5. customat RT
  6. customAfter removal of the solvent, purification

Sources & evidence

ORD record
ord-e1db6240e23147d1a90e0c067c9b6e70
Source dataset
uspto-grants-2010_02
Patent number
US07662828B2

Reaction notes

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