Trifluoroacetic acid → HCID 11633317, compound

HRID 1444600Notes

Reaction equation

HRID 1444600 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:35][CH2:34][C:18]2[N:19]=[C:20]([NH:23][C:24](=[O:33])[C:25]3[CH:30]=[CH:29][C:28]([CH2:31][CH3:32])=[CH:27][CH:26]=3)[N:21]=[CH:22][C:17]=2[CH2:16]1)=O)(C)(C)C.C(N(CC)CC)C.[S:43]1[CH:47]=[CH:46][C:45]([S:48](Cl)(=[O:50])=[O:49])=[CH:44]1>C(Cl)Cl>[CH2:31]([C:28]1[CH:27]=[CH:26][C:25]([C:24]([NH:23][C:20]2[N:21]=[CH:22][C:17]3[CH2:16][N:15]([S:48]([C:45]4[CH:46]=[CH:47][S:43][CH:44]=4)(=[O:50])=[O:49])[CH2:35][CH2:34][C:18]=3[N:19]=2)=[O:33])=[CH:30][CH:29]=1)[CH3:32]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 2776378Thiophene-3-sulfonyl ChlorideHCID 68678451HCID 68678451, compound

Product 1

HCID 11633317HCID 11633317, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Trifluoroacetic acid 7.3 ml (96 mmol) was added to a solution of 2-(4-ethyl-benzoylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylic acid tert-butyl ester 567 mg (1.48 mmol) in CH2Cl2 (10 ml) under nitrogen as inert gas and stirring was performed for 1.5 h at RT. After removal of the solvent, the intermediate (4-ethyl-N-(5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl)-benzamide trifluoroacetate) was dissolved in CH2Cl2 (10 ml). After the addition of triethylamine 1150 μl (8.20 mmol), the solution was cooled to 0° C. and 3-thiophene sulfonyl chloride 253 mg (1.39 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 4-ethyl-N-[6-(thiophene-3-sulfonyl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl]-benzamide 400 mg (0.93 mmol, 63% of theoretical) was obtained.

Workup

  1. customAfter removal of the solvent
  2. dissolutionthe intermediate (4-ethyl-N-(5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl)-benzamide trifluoroacetate) was dissolved in CH2Cl2 (10 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-b902e15aeb8e4ae1a0f61eb62b19a347
Source dataset
uspto-grants-2010_02
Patent number
US07662828B2

Reaction notes

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