N-Methylcyclohexylamine → 1-(4-(Cyclohexyl(methyl)amino)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanone

HRID 1930678Notes

Reaction equation

HRID 1930678 reaction equation
[CH3:1][NH:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.FC(F)(F)S(O[C:15]1[C:16]2[CH2:36][N:35]([C:37](=[O:39])[CH3:38])[CH2:34][CH2:33][C:17]=2[N:18]=[C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[O:32][CH:31]=[N:30][CH:29]=3)=[CH:24][CH:23]=2)[N:20]=1)(=O)=O.S(C1C=CC(C)=CC=1)([O-])(=O)=O>>[CH:3]1([N:2]([CH3:1])[C:15]2[C:16]3[CH2:36][N:35]([C:37](=[O:39])[CH3:38])[CH2:34][CH2:33][C:17]=3[N:18]=[C:19]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]4[O:32][CH:31]=[N:30][CH:29]=4)=[CH:24][CH:23]=3)[N:20]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

4

Reactant 3

HCID 7514N-MethylcyclohexylamineHCID 85570p-ToluenesulfonateHCID 593337606-Acetyl-2-(4-(oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl trifluoromethanesulfonate

Product 1

HCID 461998981-(4-(Cyclohexyl(methyl)amino)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanoneYield 17%

Procedure

1-(4-(Cyclohexyl(methyl)amino)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanone (12.6 mg, 17%) was prepared from N-methylcyclohexanamine and 6-acetyl-2-(4-(oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl trifluoromethanesulfonate according to the general procedure for amine substitution of tosylate on pyrimidines.

Sources & evidence

ORD record
ord-947033b7c9854c05abc85dfec79d12b8
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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