(R)-1,2-Epoxypropane → HCID 44818948, compound

HRID 1962148Notes

Reaction equation

HRID 1962148 reaction equation
[CH3:1][N:2]([CH3:32])[C:3]([C:5]1[N:26]([CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)[C:8]2[N:9]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)=[CH:16][N:15]=3)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4].[CH3:33][C@@H:34]1[CH2:36][O:35]1>C(O)C>[CH3:1][N:2]([CH3:32])[C:3]([C:5]1[N:26]([CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)[C:8]2[N:9]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:21][CH2:22][N:23]([CH2:33][C@H:34]([OH:35])[CH3:36])[CH2:24][CH2:25]4)=[CH:16][N:15]=3)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 146261(R)-1,2-EpoxypropaneHCID 44631912Ribociclib

Product 1

HCID 44818948HCID 44818948, compoundYield 16.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 7-cyclopentyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (55 mg, 0.123 mmol) and (R)-2-methyl-oxirane (250 mg, 4.3 mmol) in 5 mL of ethanol is heated at 70° C. for 18 h. Following SiO2 chromatography, eluting with 0-10% (2M NH3 in MeOH)/dichloromethane] gave 7-cyclopentyl-2-{5-[4-((R)-2-hydroxy-propyl)-piperazin-1-yl]-pyridin-2-ylamino}-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (10 mg, 16%). MS(ESI) m/z 493.3 (M+H)+

Workup

  1. washFollowing SiO2 chromatography, eluting with 0-10% (2M NH3 in MeOH)/dichloromethane]

Sources & evidence

ORD record
ord-5497b87449ac4cd7aaa5554ae0f26aac
Source dataset
uspto-grants-2013_04
Patent number
US08415355B2

Reaction notes

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