HCID 67313255, compound → HCID 67314727, compound

HRID 1010898Notes

Reaction equation

HRID 1010898 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH:18]([C:20]2[CH:25]=[CH:24][C:23]([C@@H:26]([NH:28][C:29]3[N:34]=[C:33]([C:35]4[N:39]5[CH:40]=[CH:41][CH:42]=[C:43]([CH3:44])[C:38]5=[N:37][CH:36]=4)[C:32]([C:45]#[N:46])=[CH:31][N:30]=3)[CH3:27])=[CH:22][CH:21]=2)[OH:19])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>O1CCCC1.CO.[OH-].[Pd+2].[OH-]>[OH:19][CH:18]([C:20]1[CH:21]=[CH:22][C:23]([C@@H:26]([NH:28][C:29]2[N:34]=[C:33]([C:35]3[N:39]4[CH:40]=[CH:41][CH:42]=[C:43]([CH3:44])[C:38]4=[N:37][CH:36]=3)[C:32]([C:45]#[N:46])=[CH:31][N:30]=2)[CH3:27])=[CH:24][CH:25]=1)[CH2:17][CH:14]1[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1

Participants

5

Reactant 1

HCID 67313255HCID 67313255, compound

Product 1

HCID 67314727HCID 67314727, compoundYield 36.5%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

21 mg of the compound [17-1] was dissolved in a mixed solvent of 3 mL of tetrahydrofuran and 3 mL of methanol, then 20 mg of a carbon catalyst of 20% palladium hydroxide was added thereto, and the mixture was stirred for 2 hours at room temperature under hydrogen atmosphere. The catalyst was filtered through celite, and the filtrate was concentrated under reduced pressure. Diethylether was added to the resulting residue, and thus produced solid was taken by filtration to obtain 6 mg of 2-({(1S)-1-[4-(1-hydroxy-2-piperidin-4-ylethyl)phenyl]ethyl}amino)-4-(8-methylimidazo[1,2-a]pyridin-3-yl)pyrimidine-5-carbonitrile [17-2] (hereinafter, referred to as the compound [17-2]).

Workup

  1. filtrationThe catalyst was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionDiethylether was added to the resulting residue, and thus produced solid
  4. filtrationwas taken by filtration

Sources & evidence

ORD record
ord-c444c0123c52409d8940ce770051258f
Source dataset
uspto-grants-2011_07
Patent number
US07977336B2

Reaction notes

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