Triethylamine → HCID 118390084, compound

HRID 1478007Notes

Reaction equation

HRID 1478007 reaction equation
Cl[C:2]1[C:3]([N:15](C)[CH:16]2[CH2:20][CH2:19][C:18]3([CH2:25][CH2:24][CH2:23][NH:22][CH2:21]3)[CH2:17]2)=[N:4][C:5]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)=[N:6][CH:7]=1.[C:27]([CH2:29][C:30]([OH:32])=O)#[N:28].[CH3:33]N(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>C(Cl)Cl.CN(C=O)C>[CH3:33][C:2]1[C:3]([NH:15][CH:16]2[CH2:24][CH2:25][C:18]3([CH2:21][N:22]([C:30](=[O:32])[CH2:29][C:27]#[N:28])[CH2:23][CH2:17]3)[CH2:19][CH2:20]2)=[N:4][C:5]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)=[N:6][CH:7]=1

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 118390117HCID 118390117, compound

Product 1

HCID 118390084HCID 118390084, compoundYield 42.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-chloro-N4-methyl-N2-(1-methyl-1H-pyrazol-4-yl)-N4-(7-azaspiro[4.5]decan-2-yl)pyrimidine-2,4-diamine (0.18 g, 0.479 mmol), 2-cyanoacetic acid (60.5 mg, 0.711 mmol) in a mixture of DCM (20 mL) and DMF (5 mL) were added HATU (335.2 mg, 0.882 mmol) and Et3N (169.4 mg, 1.674 mmol). After addition, the reaction mixture was stirred at rt overnight, then quenched with H2O (30 mL) and extracted with DCM (100 mL×3). The combined organic phases were washed with brine (100 mL), then dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=20/1) to give the title compound as a beige solid (83 mg, 39.1%).

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. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=20/1)

Sources & evidence

ORD record
ord-e580a28ef47745079dd8f46507a23ce3
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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