4-Methylmorpholine → 2-[(2-bromo-pyridin-4-ylmethyl)-amino]-N-(2-methyl-2H-indazol-6-yl)-benzamide

HRID 1434709

Reaction equation

HRID 1434709 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][NH:9][C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([OH:14])=O)[CH:5]=[CH:4][N:3]=1.[CH3:19][N:20]1[CH:28]=[C:27]2[C:22]([CH:23]=[C:24]([NH2:29])[CH:25]=[CH:26]2)=[N:21]1.CN1CCOCC1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][NH:9][C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([NH:29][C:24]2[CH:25]=[CH:26][C:27]3[C:22]([CH:23]=2)=[N:21][N:20]([CH3:19])[CH:28]=3)=[O:14])[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 5902202-Methyl-2H-indazol-6-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 231189932-[(2-Bromo-pyridin-4-ylmethyl)-amino]benzoic Acid

Product 1

HCID 231189722-[(2-bromo-pyridin-4-ylmethyl)-amino]-N-(2-methyl-2H-indazol-6-yl)-benzamideYield 96%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

0.500 g (1.6 mmol) of 2-[(2-bromo-pyridin-4-ylmethyl)-amino]-benzoic acid, 0.471 g (3.2 mmol) of 2-methyl-2H-indazol-6-ylamine, 0.4 ml (3.68 mmol) of N-methylmorpholine and 0.729 g (1.92 mmol) of O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate (HATU) in 25 ml of dimethylformamide are stirred for 16 hours at room temperature. The dimethylformamide is drawn off in an oil pump vacuum. The remaining residue is drawn off in saturated sodium bicarbonate solution. It is extracted three times with ethyl acetate, and the combined organic phases are dried, filtered and concentrated by evaporation. The residue is chromatographed on silica gel with a gradient that consists of hexane:acetone=100:0 to 50:50 as an eluant. 0.669 g (96% of theory) of 2-[(2-bromo-pyridin-4-ylmethyl)-amino]-N-(2-methyl-2H-indazol-6-yl)-benzamide is obtained in the form of a beige foam.

Workup

  1. extractionIt is extracted three times with ethyl acetate
  2. customthe combined organic phases are dried
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation
  5. customThe residue is chromatographed on silica gel with a gradient that

Sources & evidence

ORD record
ord-1427927cdc814fd3bf060e2632f8f30b
Source dataset
uspto-grants-2009_11
Patent number
US07615565B2

Linked notes

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