3'-Aminoacetophenone → HCID 46198479, compound

HRID 1930577Notes

Reaction equation

HRID 1930577 reaction equation
FC(F)(F)S(O[C:7]1[C:8]2[CH2:28][N:27]([C:29](=[O:31])[CH3:30])[CH2:26][CH2:25][C:9]=2[N:10]=[C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[O:24][CH:23]=[N:22][CH:21]=3)=[CH:16][CH:15]=2)[N:12]=1)(=O)=O.N[C:35]1[CH:36]=[C:37]([C:41](=O)C)[CH:38]=[CH:39][CH:40]=1>CS(C)=O>[CH2:41]([N:22]([CH2:21][CH2:20][OH:24])[C:7]1[C:8]2[CH2:28][N:27]([C:29](=[O:31])[CH3:30])[CH2:26][CH2:25][C:9]=2[N:10]=[C:11]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3[O:24][CH:23]=[N:22][CH:21]=3)=[CH:18][CH:19]=2)[N:12]=1)[C:37]1[CH:36]=[CH:35][CH:40]=[CH:39][CH:38]=1

Participants

4

Reactant 2

HCID 74173'-AminoacetophenoneHCID 593337606-Acetyl-2-(4-(oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl trifluoromethanesulfonate

Product 1

HCID 46198479HCID 46198479, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

6-Acetyl-2-(4-(oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl trifluoromethanesulfonate (35 mg, 0.07 mmol, Example 26a) in DMSO (1 mL) was dispensed in a library plate. 1-(3-aminophenyl)ethanone (-, 0.07 mmol) was added and it was left to shake overnight at 80° C. before filtered and purified by preparative HPLC to yield 1-(4-(benzyl(2-hydroxyethyl)amino)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanone (16.5 mg, 49%).

Workup

  1. waitit was left
  2. filtrationbefore filtered
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-ee060529c99943b19b24a635e9f81e8d
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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