3-(Cyclopropylamino)propionitrile → 3-((6-Acetyl-2-(4-(oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(cyclopropyl)amino)propanenitrile

HRID 1930576Notes

Reaction equation

HRID 1930576 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([NH:37][CH2:38][CH2:39][C:40]#[N:41])[CH2:36][CH2:35]1>CS(C)=O>[C:29]([N:27]1[CH2:26][CH2:25][C:9]2[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]=[C:7]([N:37]([CH:34]3[CH2:36][CH2:35]3)[CH2:38][CH2:39][C:40]#[N:41])[C:8]=2[CH2:28]1)(=[O:31])[CH3:30]

Participants

4

Reactant 2

HCID 1435373-(Cyclopropylamino)propionitrileHCID 593337606-Acetyl-2-(4-(oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl trifluoromethanesulfonate

Product 1

HCID 461984783-((6-Acetyl-2-(4-(oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(cyclopropyl)amino)propanenitrileYield 49.9%

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. 3-(cyclopropylamino)propanenitrile (7.71 mg, 0.07 mmol) was added and it was left to shake overnight at 80° C. before filtered and purified by preparative HPLC to yield 3-((6-Acetyl-2-(4-(oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(cyclopropyl)amino)propanenitrile (15.5 mg, 48%).

Workup

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

Sources & evidence

ORD record
ord-9d0cb9de8ec642af858fbcd8bbb5a420
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

Loading…