Cyclopropanecarbonyl chloride → cyclopropyl(4-((2-hydroxyethyl)(phenyl)amino)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)methanone

HRID 1930560Notes

Reaction equation

HRID 1930560 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.[CH:33]1([C:36](Cl)=[O:37])[CH2:35][CH2:34]1>CN(C=O)C>[CH:33]1([C:36]([N:21]2[CH2:20][CH2:19][C:17]3[N:18]=[C:13]([NH:12][C:9]4[CH:10]=[CH:11][C:6]([C:5]5[O:1][CH:2]=[N:3][CH:4]=5)=[CH:7][CH:8]=4)[N:14]=[C:15]([N:23]([CH2:24][CH2:25][OH:26])[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:16]=3[CH2:22]2)=[O:37])[CH2:35][CH2:34]1

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chloride2×HCID 462000502-((2-(4-(Oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanol

Product 1

HCID 46200511cyclopropyl(4-((2-hydroxyethyl)(phenyl)amino)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)methanoneYield 3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-((2-(4-(Oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanol (50 mg, 0.12 mmol, Example 1) was dissolved in DMF (3 mL). Cyclopropanecarbonyl chloride (10.59 μL, 0.12 mmol) was added and the reaction was stirred at room temperature for 4 h. An extra equivalent of cyclopropanecarbonyl chloride was added and the reaction was stirred for 2 h. The solvent was evaporated, the crude dissolved in few drops dimethylformamide and acetonitrile, filtered and purified by preparative HPLC yielding cyclopropyl(4-((2-hydroxyethyl)(phenyl)amino)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)methanone (1.8 mg, 2.96%).

Workup

  1. stirringthe reaction was stirred for 2 h
  2. customThe solvent was evaporated
  3. dissolutionthe crude dissolved in few drops dimethylformamide and acetonitrile
  4. filtrationfiltered
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-54dcc148b7334777a40644ffedbe797a
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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