Triethylamine → HCID 118390064, compound

HRID 1477998Notes

Reaction equation

HRID 1477998 reaction equation
[Cl:1][C:2]1[C:3]([NH:15][CH:16]2[C:20]3([CH2:24][CH2:23][CH2:22][CH2:21]3)[CH2:19][NH: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:25]([CH2:27][C:28](O)=[O:29])#[N:26].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.O>[Cl:1][C:2]1[C:3]([NH:15][CH:16]2[C:20]3([CH2:21][CH2:22][CH2:23][CH2:24]3)[CH2:19][N:18]([C:28](=[O:29])[CH2:27][C:25]#[N:26])[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

8

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 118390053HCID 118390053, compound

Product 1

HCID 118390064HCID 118390064, compoundYield 61.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-chloro-N2-(1-methyl-1H-pyrazol-4-yl)-N4-(2-azaspiro[4.4]nonan-4-yl)pyrimidine-2,4-diamine (393 mg, 1.13 mmol), 2-cyanoacetic acid (240.83 mg, 2.83 mmol), HATU (429.63 g, 1.13 mmol) in a mixture of DCM and DMF (4/1 (v/v), 25 mL) was added Et3N (456.52 mg, 4.52 mmol) and the reaction mixture was stirred at rt for 3 hours. The resulting mixture was diluted with H2O (20 mL) and extracted with a mixture of DCM and MeOH (10/1 (v/v), 20 mL×3). The combined organic phases were washed with brine (50 mL), and dried over anhydrous Na2SO4, then concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH=100/1 to 20/1) to give the product as a white solid (290 mg, 61.8%).

Workup

  1. extractionextracted with a mixture of DCM and MeOH (10/1 (v/v), 20 mL×3)
  2. washThe combined organic phases were washed with brine (50 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (DCM/MeOH=100/1 to 20/1)

Sources & evidence

ORD record
ord-aa297efca8cb4a948c913bd05f2d87b3
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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