4-Methylmorpholine → HCID 58103041, compound

HRID 2178614Notes

Reaction equation

HRID 2178614 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=O)[CH:3]=1.[CH:11]1([N:14]2[C:18]([C:19]3[N:24]=[C:23]([NH2:25])[CH:22]=[CH:21][CH:20]=3)=[CH:17][N:16]=[CH:15]2)[CH2:13][CH2:12]1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.CN1CCOCC1>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:25][C:23]2[CH:22]=[CH:21][CH:20]=[C:19]([C:18]3[N:14]([CH:11]4[CH2:13][CH2:12]4)[CH:15]=[N:16][CH:17]=3)[N:24]=2)=[O:10])[CH:3]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 2308904-Chloropyridine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66851773HCID 66851773, compound

Product 1

HCID 58103041HCID 58103041, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-chloro-pyridine-2-carboxylic acid (141 mg, 0.895 mmol), 6-(3-cyclopropyl-3H-imidazol-4-yl)-pyridin-2-ylamine (150 mg, 0.750 mmol), (2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU) (342 g, 0.899 mmol), and N-methylmorpholine (250 μL, 2.70 mmol) in N,N-dimethylformamide was stirred at room temperature for 12 hours. The solvent was removed under reduced pressure, the residue suspended in acetonitrile, and the solid isolated by filtration, washed with water (80 mL), acetonitrile (80 mL) and diethyl ether (80 mL), and dried under reduced pressure to afford 4-chloro-N-(6-(1-cyclopropyl-1H-imidazol-5-yl)pyridin-2-yl)picolinamide as a white powder (120 mg, 47% yield). M+1=340.1

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe solid isolated by filtration
  3. washwashed with water (80 mL), acetonitrile (80 mL) and diethyl ether (80 mL)
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-a2d35e1e064444cfa7c7ff96639ce7e0
Source dataset
uspto-grants-2015_06
Patent number
US09067933B2

Reaction notes

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