4-Methylmorpholine → 4-chloro-N-(6-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-yl)-5-methylpicolinamide

HRID 1040239Notes

Reaction equation

HRID 1040239 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([C:9]([OH:11])=O)[CH:3]=1.[CH:12]1([N:15]2[CH:19]=[N:18][N:17]=[C:16]2[C:20]2[N:25]=[C:24]([NH2:26])[CH:23]=[CH:22][CH:21]=2)[CH2:14][CH2:13]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[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([C:9]([NH:26][C:24]2[CH:23]=[CH:22][CH:21]=[C:20]([C:16]3[N:15]([CH:12]4[CH2:14][CH2:13]4)[CH:19]=[N:18][N:17]=3)[N:25]=2)=[O:11])[CH:3]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 534400144-Chloro-5-methylpyridine-2-carboxylic acidHCID 581029666-(4-Cyclopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-amine

Product 1

HCID 581029954-chloro-N-(6-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-yl)-5-methylpicolinamideYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-chloro-5-methylpicolinic acid (159 mg, 0.924 mmol), 6-(4-Cyclopropyl-4H-[1,2,4]triazol-3-yl)-pyridin-2-ylamine (169 mg, 0.840 mmol), (2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU) (383 mg, 1.01 mmol), and N-methylmorpholine (11 μL, 1.01 mmol) in N,N-dimethylformamide was stirred at 65° C. for 1.2 hours. The solvent was removed under reduced pressure, the residue was suspended in acetonitrile, and the solid product was isolated by filtration, washed with water (80 mL), acetonitrile (80 mL), diethyl ether (80 mL), and dried under vacuum to afford 4-chloro-N-(6-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-yl)-5-methylpicolinamide as a white powder (140 mg, 47% yield).

Workup

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

Sources & evidence

ORD record
ord-fc5bc608604c469fb043c70de41780b6
Source dataset
uspto-grants-2013_10
Patent number
US08552196B2

Reaction notes

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