Cyclohexylamine → HCID 46200835, compound

HRID 1930570Notes

Reaction equation

HRID 1930570 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.[CH:34]1([NH2:40])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>CS(C)=O>[CH:34]1([NH:40][C:7]2[C:8]3[CH2:28][N:27]([C:29](=[O:31])[CH3:30])[CH2:26][CH2:25][C:9]=3[N:10]=[C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[O:24][CH:23]=[N:22][CH:21]=4)=[CH:16][CH:15]=3)[N:12]=2)[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 593337606-Acetyl-2-(4-(oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl trifluoromethanesulfonate

Product 1

HCID 46200835HCID 46200835, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

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) in DMSO (1 mL) was dispensed in a library plate. Cyclohexanamine (6.94 mg, 0.07 mmol) was added and the reaction mixture was stirred overnight at 80° C. before it was filtered and purified by preparative HPLC to give 1-(4-(cyclohexylamino)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanone (11.2 mg, 36%).

Workup

  1. filtrationwas filtered
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-48af044e59e844b994f7a956b95e9747
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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