1,1'-Carbonyldiimidazole → HCID 68687123, compound

HRID 2238658Notes

Reaction equation

HRID 2238658 reaction equation
[C:1]([C:3]1[C:4]([C:21]2[N:25]3[CH:26]=[CH:27][CH:28]=[C:29]([CH:30]([F:32])[F:31])[C:24]3=[N:23][CH:22]=2)=[N:5][C:6]([NH:9][CH:10]([C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=2)[C:15](O)=[O:16])[CH3:11])=[N:7][CH:8]=1)#[N:2].C1N=CN(C(N2C=NC=C2)=O)C=1.[Na].C(=O)([O-])O.[Na+]>O1CCCC1>[F:32][CH:30]([F:31])[C:29]1[C:24]2[N:25]([C:21]([C:4]3[C:3]([C:1]#[N:2])=[CH:8][N:7]=[C:6]([NH:9][CH:10]([C:12]4[CH:20]=[CH:19][CH:18]=[C:14]([CH2:15][OH:16])[CH:13]=4)[CH3:11])[N:5]=3)=[CH:22][N:23]=2)[CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 68686803HCID 68686803, compound

Product 1

HCID 68687123HCID 68687123, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

151 mg of the 3-[1-({5-cyano-4-[8-(difluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl}amino)ethyl] benzoic acid [100-4] was dissolved in 4 mL of tetrahydrofuran, then 282 mg of N,N-carbonyldiimidazole was added, and stirred overnight at room temperature. The reaction mixture was added with 132 mg of sodium boronhydride in two additions, and stirred at room temperature for 30 minutes. Thereto, a saturated aqueous solution of sodium hydrogen carbonate was added, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the thus obtained residue was purified by preparative thin-layer chromatography, to obtain 50 mg of 4-[8-(difluoromethyl)imidazo[1,2-a]pyridin-3-yl]-2-({1-[3-(hydroxymethyl)phenyl)ethyl}amino)pyrimidin-5-carbonitrile [101-1] as a pale yellow oily product.

Workup

  1. stirringstirred at room temperature for 30 minutes
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe insolubles were filtered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe thus obtained residue was purified by preparative thin-layer chromatography

Sources & evidence

ORD record
ord-fda19d808f8e465a9b0b60efe3d1171b
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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