Triethylamine → HCID 118390084, compound

HRID 1477980Notes

Reaction equation

HRID 1477980 reaction equation
[CH3:1][C:2]1[C:3]([NH:15][CH:16]2[CH2:25][CH2:24][C:19]3([CH2:23][NH:22][CH2:21][CH2:20]3)[CH2:18][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:26]([CH2:28][C:29](O)=[O:30])#[N:27].CN(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>[CH3:1][C:2]1[C:3]([NH:15][CH:16]2[CH2:25][CH2:24][C:19]3([CH2:23][N:22]([C:29](=[O:30])[CH2:28][C:26]#[N:27])[CH2:21][CH2:20]3)[CH2:18][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

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 118390004HCID 118390004, compound

Product 1

HCID 118390084HCID 118390084, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-methyl-N2-(1-methyl-1H-pyrazol-4-yl)-N4-(2-azaspiro[4.5]decan-8-yl)pyrimidine-2,4-diamine (186 mg, 0.545 mmol), 2-cyanoacetic acid (48.4 mg, 0.569 mmol) in a mixture of DCM (32 mL) and DMF (8 mL) were added HATU (423.4 mg, 1.087 mmol) and Et3N (0.21 g, 2.075 mmol). After addition, the reaction mixture was stirred at rt for 2 h, 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 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 beige solid (170 mg, 76.4%).

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)=10/1)

Sources & evidence

ORD record
ord-aaafcf41036b433c9069f501248e4b09
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

Loading…