L-Alaninol → HCID 11327216, compound

HRID 2353307Notes

Reaction equation

HRID 2353307 reaction equation
[F:1][C:2]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:3]=1[O:4][C:5]1[C:18](=[O:19])[N:17]([CH2:20][C@@H:21]([OH:23])[CH3:22])[C:8]2[N:9]=[C:10](S(C)(=O)=O)[N:11]=[CH:12][C:7]=2[CH:6]=1.[NH2:29][C@@H:30]([CH3:33])[CH2:31][OH:32]>O1CCCC1>[F:1][C:2]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:3]=1[O:4][C:5]1[C:18](=[O:19])[N:17]([CH2:20][C@@H:21]([OH:23])[CH3:22])[C:8]2[N:9]=[C:10]([NH:29][C@@H:30]([CH3:33])[CH2:31][OH:32])[N:11]=[CH:12][C:7]=2[CH:6]=1

Participants

4

Reactant 2

HCID 80307L-AlaninolHCID 59681440HCID 59681440, compound

Product 1

HCID 11327216HCID 11327216, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran (5 mL) solution of 6-(2,4-difluorophenoxy)-8-((S)-2-hydroxypropyl)-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one (400 mg, 1 mmol) was added (S)-2-amino-1-propanol (0.38 mL, 5 mmol) and stirred overnight at room temperature. Concentrated under vacuum and chromatographed on silica gel eluding with 2% methanol in dichloromethane and converted to the hydrochloride salt to give 320 mg 6-(2,4-difluoro-phenoxy)-2-((S)-(+)-2-hydroxy-1-methyl-ethylamino)-8-((S)-2-hydroxy-propyl)-8H-pyrido[2,3-d]pyrimidin-7-one (mass spec. M+1=407, MP=175.1-179.1° C.).

Workup

  1. concentrationConcentrated under vacuum
  2. customchromatographed on silica gel eluding with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-8bc6223a23494bc4b55192d19229c141
Source dataset
uspto-grants-2010_07
Patent number
US07750016B2

Reaction notes

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