Butyric Acid → HCID 59834639, compound

HRID 271564Notes

Reaction equation

HRID 271564 reaction equation
[C:1]([OH:6])(=O)[CH2:2][CH2:3][CH3:4].[CH3:7][C:8]([CH3:29])([CH3:28])[CH2:9][N:10]1[C:14]2[N:15]=[C:16]([C:19]#[N:20])[N:17]=[CH:18][C:13]=2[CH:12]=[C:11]1[CH2:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C1C=CC2N(O)N=NC=2C=1.Cl.[Cl-].[NH4+]>CN(C=O)C>[C:1]([N:25]1[CH2:26][CH2:27][N:22]([CH2:21][C:11]2[N:10]([CH2:9][C:8]([CH3:29])([CH3:28])[CH3:7])[C:14]3[N:15]=[C:16]([C:19]#[N:20])[N:17]=[CH:18][C:13]=3[CH:12]=2)[CH2:23][CH2:24]1)(=[O:6])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 5

HCID 264Butyric AcidHCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 59834726HCID 59834726, compound

Product 1

HCID 59834639HCID 59834639, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Butyric acid (0.35 mmol) and 7-(2,2-dimethyl-propyl)-6-piperazin-1-ylmethyl-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile (0.29 mmol) are dissolved in DMF (10 ml) and cooled with ice. HOBt (0.42 mmol) and WSCD.HCl (0.42 mmol) are added to the cold solution, and the reaction mixture is stirred at 4° C.-25° C. overnight. After saturated ammonium chloride is added to the reaction mixture, the mixture is extracted with AcOEt. The organic layer is washed with saturated ammonium chloride and brine, dried over magnesium sulfate and evaporated down. The crude product is applied to silica gel column chromatography, which is eluted with following solvents: n-hexane:AcOEt=1:1 (v/v), n-hexane:AcOEt=1:4 (v/v) and n-hexane:AcOEt=1:9 (v/v). The solvent of the latter effluent is removed by evaporation and dried in vacuo to afford the title compound. yield 43.2%, Rf=0.19 (n-hexane:AcOEt=1:5).

Workup

  1. temperaturecooled with ice
  2. extractionthe mixture is extracted with AcOEt
  3. washThe organic layer is washed with saturated ammonium chloride and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated down
  6. washis eluted with following solvents
  7. customThe solvent of the latter effluent is removed by evaporation
  8. customdried in vacuo

Sources & evidence

ORD record
ord-9ea0a9ceba2446e6b4763b062b475578
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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