Triethylamine → HCID 118389995, compound

HRID 1478087Notes

Reaction equation

HRID 1478087 reaction equation
CN1C=CC([NH:7][C:8]2[N:13]=[C:12]([NH:14][CH:15]3[CH2:22][CH:18]4[CH2:19][NH:20][CH2:21][CH:17]4[CH2:16]3)[C:11]([C:23]#[N:24])=[CH:10][N:9]=2)=N1.[C:25]([CH2:27][C:28]([OH:30])=O)#[N:26].CN(C(ON1[N:47]=[N:46][C:41]2[CH:42]=[CH:43]C=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:55](N(CC)CC)C>ClCCl.CN(C)C=O>[C:25]([CH2:27][C:28]([N:20]1[CH2:19][CH:18]2[CH2:22][CH:15]([NH:14][C:12]3[C:11]([C:23]#[N:24])=[CH:10][N:9]=[C:8]([NH:7][C:42]4[CH:41]=[N:46][N:47]([CH3:55])[CH:43]=4)[N:13]=3)[CH2:16][CH:17]2[CH2:21]1)=[O:30])#[N:26]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9740Cyanoacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118390088HCID 118390088, compound

Product 1

HCID 118389995HCID 118389995, compoundYield 18.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-((1-methyl-1H-pyrazol-3-yl)amino)-4-((octahydrocyclopenta[c]pyrrol-5-yl)amino)pyrimidine-5-carbonitrile (165.2 mg, 0.5092 mmol) and 2-cyanoacetic acid (65 mg, 0.7642 mmol) in dichloromethane (20 mL) and N,N-dimethylformamide (5 mL) were added HATU (387.5 mg, 1.019 mmol) and N,N-diethylethanamine (103.5 mg, 1.023 mmol). The mixture was then stirred at rt for 1 h and then quenched with H2O (20 mL), and the resulted mixture was extracted with DCM/MeOH (10/1, 20 mL×3). The combined organic phases were washed with brine (50 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=10/1) to give the title compound as a white solid (36 mg, 18.06%).

Workup

  1. customquenched with H2O (20 mL)
  2. extractionthe resulted mixture was extracted with DCM/MeOH (10/1, 20 mL×3)
  3. washThe combined organic phases were washed with brine (50 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=10/1)

Sources & evidence

ORD record
ord-0c4e89030fd045b5bcbc5f342792a1ca
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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