HCID 59553907, compound → HCID 59553890, compound

HRID 1170927Notes

Reaction equation

HRID 1170927 reaction equation
C([O:8][C:9]1[C:10]([CH:15]2[NH:20][C:19]3[CH:21]=[CH:22][N:23]=[C:24]([C:25]([F:28])([F:27])[F:26])[C:18]=3[C:17](=[O:29])[N:16]2[CH:30]([CH3:40])[CH2:31][C:32]2[CH:37]=[CH:36][C:35]([F:38])=[C:34]([F:39])[CH:33]=2)=[N:11][CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>C(O)C>[F:39][C:34]1[CH:33]=[C:32]([CH2:31][CH:30]([N:16]2[C:17](=[O:29])[C:18]3[C:24]([C:25]([F:26])([F:27])[F:28])=[N:23][CH:22]=[CH:21][C:19]=3[NH:20][CH:15]2[C:10]2[C:9]([OH:8])=[CH:14][CH:13]=[CH:12][N:11]=2)[CH3:40])[CH:37]=[CH:36][C:35]=1[F:38]

Participants

3

Reactant 1

HCID 59553907HCID 59553907, compound

Product 1

HCID 59553890HCID 59553890, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(3-(benzyloxy)pyridin-2-yl)-3-(1-(3,4-difluorophenyl)propan-2-yl)-5-(trifluoromethyl)-2,3-dihydropyrido[4,3-d]pyrimidin-4(1H)-one (12.1 grams, 21.8 mmol) prepared by the same reactions conditions described above was dissolved in 300 mL of ethanol and added to a parr bottle that contained 10% Pd(C). The mixture was subjected to hydrogenation condition (45 psi) for two hours. At this time, the reaction mixture was filtered through Celite and washed with ethanol. The fitrate was concentrated in vacuo and purified by silica gel chromatography to afford a pale yellow foam of 3-(1-(3,4-difluorophenyl)propan-2-yl)-2-(3-hydroxypyridin-2-yl)-5-(trifluoromethyl)-2,3-dihydropyrido[4,3-d]pyrimidin-4(1H)-one.

Workup

  1. additionadded to a parr bottle
  2. filtrationAt this time, the reaction mixture was filtered through Celite
  3. washwashed with ethanol
  4. concentrationThe fitrate was concentrated in vacuo
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-1b223c3efd6945808434dcc26b4eb83d
Source dataset
uspto-grants-2010_11
Patent number
US07829572B2

Reaction notes

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