Sodium Hydroxide → HCID 67314192, compound

HRID 1010908Notes

Reaction equation

HRID 1010908 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([C:11]3[C:16]([C:17]#[N:18])=[CH:15][N:14]=[C:13]([NH:19][C@H:20]([C:22]4[CH:27]=[CH:26][C:25]([CH:28]([OH:41])[CH:29]5[CH2:34][CH2:33][N:32](C(=O)C(F)(F)F)[CH2:31][CH2:30]5)=[CH:24][CH:23]=4)[CH3:21])[N:12]=3)=[CH:9][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>O1CCCC1.CO>[Cl:1][C:2]1[C:3]2[N:4]([C:8]([C:11]3[C:16]([C:17]#[N:18])=[CH:15][N:14]=[C:13]([NH:19][C@H:20]([C:22]4[CH:27]=[CH:26][C:25]([CH:28]([OH:41])[CH:29]5[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]5)=[CH:24][CH:23]=4)[CH3:21])[N:12]=3)=[CH:9][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86625218HCID 86625218, compound

Product 1

HCID 67314192HCID 67314192, compoundYield 78.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

237 mg of the compound [37-3] was dissolved in a mixed solvent of 3 mL of tetrahydrofuran and 1 mL of methanol, then 163 μL of 5N aqueous solution of sodium hydroxide was added thereto, and the mixture was stirred for 5 hours at 50° C. After standing to cool, the reaction solution was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: chloroform/methanol=95/5-93/7), to obtain 156 mg of 4-(8-chloroimidazo[1,2-a]pyridin-3-yl)-2-[((1S)-1-{4-[hydroxy(piperidin-4-yl)methyl]phenyl}ethyl)amino]pyrimidine-5-carbonitrile [374] (hereinafter, referred to as the compound [374]).

Workup

  1. temperatureto cool
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography (eluent: chloroform/methanol=95/5-93/7)

Sources & evidence

ORD record
ord-9f978bd0519d4395ba840b2fade54735
Source dataset
uspto-grants-2011_07
Patent number
US07977336B2

Reaction notes

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