Triethylamine → HCID 46200355, compound

HRID 1930559Notes

Reaction equation

HRID 1930559 reaction equation
[O:1]1[C:5]([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13]3[N:14]=[C:15]([N:23]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:24][CH2:25][OH:26])[C:16]4[CH2:22][NH:21][CH2:20][CH2:19][C:17]=4[N:18]=3)=[CH:8][CH:7]=2)=[CH:4][N:3]=[CH:2]1.C(N(CC)CC)C.[C:40](Cl)(=[O:43])[CH2:41][CH3:42]>CN(C=O)C.ClCCl>[OH:26][CH2:25][CH2:24][N:23]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:15]1[C:16]2[CH2:22][N:21]([C:40](=[O:43])[CH2:41][CH3:42])[CH2:20][CH2:19][C:17]=2[N:18]=[C:13]([NH:12][C:9]2[CH:10]=[CH:11][C:6]([C:5]3[O:1][CH:2]=[N:3][CH:4]=3)=[CH:7][CH:8]=2)[N:14]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 462000502-((2-(4-(Oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanol

Product 1

HCID 46200355HCID 46200355, compoundYield 8.32%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

2-((2-(4-(Oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanol (85 mg, 0.20 mmol, Example 1) was dissolved in DMF (0.5 mL) and dichloromethane (4 mL). Triethylamine (0.028 mL, 0.20 mmol) was added followed by propionyl chloride (0.021 mL, 0.24 mmol). The reaction mixture was stirred at room temperature for 2 h and the solvent was evaporated under reduced pressure. The crude was dissolved in dimethylformamide and acetonitrile, filtered and purified by preparative HPLC yielding 1-(4-((2-hydroxyethyl)(phenyl)amino)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)propan-1-one (8.0 mg, 8.32%).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionThe crude was dissolved in dimethylformamide
  3. filtrationacetonitrile, filtered
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-4589c62d97f24777be020d06ec1937ba
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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