1-Aminocyclopentanemethanol → 1-(4-(1-(hydroxymethyl)cyclopentylamino)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanone

HRID 1930580Notes

Reaction equation

HRID 1930580 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.[NH2:34][C:35]1([CH2:40][OH:41])[CH2:39][CH2:38][CH2:37][CH2:36]1>CS(C)=O>[OH:41][CH2:40][C:35]1([NH:34][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:15]=[CH:16][C:17]([C:20]4[O:24][CH:23]=[N:22][CH:21]=4)=[CH:18][CH:19]=3)[N:12]=2)[CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

4

Reactant 2

HCID 663071-AminocyclopentanemethanolHCID 593337606-Acetyl-2-(4-(oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl trifluoromethanesulfonate

Product 1

HCID 461984821-(4-(1-(hydroxymethyl)cyclopentylamino)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanoneYield 27.1%

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) dispensed in a library plate. (1-aminocyclopentyl)methanol (8.06 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 1-(4-(1-(hydroxymethyl)cyclopentylamino)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanone (8.5 mg, 26%).

Workup

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

Sources & evidence

ORD record
ord-38a6a1f8d10542018b0f214d1813f579
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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