(2R)-2,3-dihydro-1H-indol-2-ylmethanol → (R)-1-(4-(2-(Hydroxymethyl)indolin-1-yl)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanone

HRID 1930582Notes

Reaction equation

HRID 1930582 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.[NH:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH2:36][C@@H:35]1[CH2:43][OH:44]>CS(C)=O>[OH:44][CH2:43][C@H:35]1[CH2:36][C:37]2[C:42](=[CH:41][CH:40]=[CH:39][CH:38]=2)[N:34]1[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

Participants

4

Reactant 2

HCID 6951187(2R)-2,3-dihydro-1H-indol-2-ylmethanolHCID 593337606-Acetyl-2-(4-(oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl trifluoromethanesulfonate

Product 1

HCID 46198654(R)-1-(4-(2-(Hydroxymethyl)indolin-1-yl)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanoneYield 37.6%

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. (R)-indolin-2-ylmethanol (10.44 mg, 0.07 mmol) was added to it and the reaction mixture was left to shake overnight at 80° C. before filtered and purified by preparative HPLC to yield (R)-1-(4-(2-(Hydroxymethyl)indolin-1-yl)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanone (12.7 mg, 36%).

Workup

  1. waitthe reaction mixture was left
  2. filtrationbefore filtered
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-3424c3ab2c4c4380947f2b10c6b4cc6c
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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