Cyanoacetic acid → HCID 118390166, compound

HRID 1056647Notes

Reaction equation

HRID 1056647 reaction equation
[CH3:1][N:2]1[C:10]([CH3:11])=[C:9]2[C:4]([CH:5]=[C:6]([NH:12][C:13]3[N:18]=[C:17]([NH:19][CH:20]4[CH2:27][CH:23]5[CH2:24][NH:25][CH2:26][CH:22]5[CH2:21]4)[C:16]([CH3:28])=[CH:15][N:14]=3)[CH:7]=[CH:8]2)=[N:3]1.[C:29]([CH2:31][C:32](O)=[O:33])#[N:30].C1C=NC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C=O)C>[CH3:1][N:2]1[C:10]([CH3:11])=[C:9]2[C:4]([CH:5]=[C:6]([NH:12][C:13]3[N:18]=[C:17]([NH:19][CH:20]4[CH2:27][CH:23]5[CH2:24][N:25]([C:32](=[O:33])[CH2:31][C:29]#[N:30])[CH2:26][CH:22]5[CH2:21]4)[C:16]([CH3:28])=[CH:15][N:14]=3)[CH:7]=[CH:8]2)=[N:3]1

Participants

7

Reactant 4

HCID 9740Cyanoacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 118406569HCID 118406569, compound

Product 1

HCID 118390166HCID 118390166, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of N2-(2,3-dimethyl-2H-indazol-6-yl)-5-methyl-N4-(octahydrocyclopenta[c]pyrrol-5-yl)pyrimidine-2,4-diamine (86.9 mg, 0.23 mmol) and 2-cyanoacetic acid (31.3 mg, 0.37 mmol) in a mixture of DCM (8 mL) and DMF (2 mL) were added HOAT (65.5 mg, 0.48 mmol) and EDCI (77.6 mg, 0.40 mmol). After addition, the reaction mixture was stirred at 45° C. for 1 h, and then quenched with H2O (30 mL) and extracted with DCM (100 mL×3). The combined organic phases were washed with brine (100 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/10) to give the title compound as a beige solid (69.8 mg, 68.2%).

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)=1/10)

Sources & evidence

ORD record
ord-f511aa910116418db342c8cb372eba90
Source dataset
uspto-grants-2016_07
Patent number
US09399637B2

Reaction notes

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