Cyanoacetic acid → HCID 118390101, compound

HRID 1478070Notes

Reaction equation

HRID 1478070 reaction equation
[Cl:1][C:2]1[C:3]([NH:18][CH:19]2[CH2:26][CH:22]3[CH2:23][NH:24][CH2:25][CH:21]3[CH2:20]2)=[N:4][C:5]([NH:8][C:9]2[N:13]([CH3:14])[N:12]=[C:11]([CH:15]3[CH2:17][CH2:16]3)[CH:10]=2)=[N:6][CH:7]=1.[C:27]([CH2:29][C:30](O)=[O:31])#[N:28].CCN=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[C:3]([NH:18][CH:19]2[CH2:26][CH:22]3[CH2:23][N:24]([C:30](=[O:31])[CH2:29][C:27]#[N:28])[CH2:25][CH:21]3[CH2:20]2)=[N:4][C:5]([NH:8][C:9]2[N:13]([CH3:14])[N:12]=[C:11]([CH:15]3[CH2:17][CH2:16]3)[CH:10]=2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 9740Cyanoacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 118390022HCID 118390022, compound

Product 1

HCID 118390101HCID 118390101, compoundYield 57.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 5-chloro-N2-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-N4-(octahydrocyclopenta[c]pyrrol-5-yl)pyrimidine-2,4-diamine (251.7 mg, 0.67 mmol) and 2-cyanoacetic acid (107.2 mg, 1.26 mmol) in a mixture of DCM (20 mL) and DMF (5 mL) were added EDCI (292.5 mg, 1.51 mmol) and HOAT (205.3 mg, 1.51 mmol). After addition, the reaction mixture was stirred at 45° C. for 1 h, then quenched with H2O (30 mL) and extracted with DCM (100 mL×3). The combined organic phases were washed with brine (100 mL), and dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/40) to give the title compound as a beige solid (169.4 mg, 57.1%).

Workup

  1. additionAfter addition
  2. customquenched with H2O (30 mL)
  3. extractionextracted with DCM (100 mL×3)
  4. washThe combined organic phases were washed with brine (100 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/40)

Sources & evidence

ORD record
ord-1d721d1511be450383a3d40ed3246d86
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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