L-Tartaric acid → Methyl 2-[4-({[2-[2-(2,3-difluorophenyl)ethyl]-4-oxopyrido[2,3-d]pyrimidin-1(4H)-yl]-acetyl}{[4'-(trifluoromethyl)-4-biphenylyl]methyl}amino)-1-piperidinyl]-2-methylpropanoate 2,3-dihydroxybutanedioate

HRID 1855638Notes

Reaction equation

HRID 1855638 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]1[N:16]([CH2:17][C:18]([N:20]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]3[CH:46]=[CH:45][C:44]([C:47]([F:50])([F:49])[F:48])=[CH:43][CH:42]=3)=[CH:37][CH:36]=2)[CH:21]2[CH2:26][CH2:25][N:24]([C:27]([CH3:33])([CH3:32])[C:28]([O:30][CH3:31])=[O:29])[CH2:23][CH2:22]2)=[O:19])[C:15]2[N:51]=[CH:52][CH:53]=[CH:54][C:14]=2[C:13](=[O:55])[N:12]=1.[C:56]([OH:65])(=[O:64])[C@@H:57]([C@H:59]([C:61]([OH:63])=[O:62])[OH:60])[OH:58]>CO>[OH:60][CH:59]([CH:57]([OH:58])[C:56]([OH:65])=[O:64])[C:61]([OH:63])=[O:62].[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]1[N:16]([CH2:17][C:18]([N:20]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]3[CH:42]=[CH:43][C:44]([C:47]([F:50])([F:48])[F:49])=[CH:45][CH:46]=3)=[CH:37][CH:36]=2)[CH:21]2[CH2:22][CH2:23][N:24]([C:27]([CH3:32])([CH3:33])[C:28]([O:30][CH3:31])=[O:29])[CH2:25][CH2:26]2)=[O:19])[C:15]2[N:51]=[CH:52][CH:53]=[CH:54][C:14]=2[C:13](=[O:55])[N:12]=1

Participants

4

Reactant 2

HCID 444305L-Tartaric acidHCID 24771862Methyl 2-[4-({[2-[2-(2,3-difluorophenyl)ethyl]-4-oxopyrido[2,3-d]pyrimidin-1(4H)-yl]-acetyl}{[4'-(trifluoromethyl)-4-biphenylyl]methyl}amino)-1-piperidinyl]-2-methylpropanoate

Product 1

HCID 24812263Methyl 2-[4-({[2-[2-(2,3-difluorophenyl)ethyl]-4-oxopyrido[2,3-d]pyrimidin-1(4H)-yl]-acetyl}{[4'-(trifluoromethyl)-4-biphenylyl]methyl}amino)-1-piperidinyl]-2-methylpropanoate 2,3-dihydroxybutanedioate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 2-[4-({[2-[2-(2,3-difluorophenyl)ethyl]-4-oxopyrido[2,3-d]pyrimidin-1(4H)-yl]-acetyl}{[4′-(trifluoromethyl)-4-biphenylyl]methyl}amino)-1-piperidinyl]-2-methylpropanoate (8.5 g, 1 equiv) was suspended in methanol (100 ml) and warmed to 50° C. until the solid dissolved. L-Tartaric acid (1.675 g, 1.0 equiv) was added in one portion and stirred for 30 minutes at room temperature. The solution was concentrated in vacuo to an off-white powder that was dried in a vacuum oven at room temperature.

Workup

  1. dissolutiondissolved
  2. concentrationThe solution was concentrated in vacuo to an off-white powder that
  3. customwas dried in a vacuum oven at room temperature

Sources & evidence

ORD record
ord-62ab65fdf7f748a5b6801a62741d341d
Source dataset
uspto-grants-2015_02
Patent number
US08962633B2

Reaction notes

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