4-Methylmorpholine → 4-[6-Amino-5-(pyridin-4-ylcarbamoyl)-pyridin-3-yl]-2-fluoro-benzoic acid

HRID 919263Notes

Reaction equation

HRID 919263 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:17](=[O:25])[NH:18][C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1.COCCNC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.[F:49][P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:12]([OH:14])=[O:13])=[C:15]([F:49])[CH:16]=2)=[CH:4][C:3]=1[C:17](=[O:25])[NH:18][C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 300977(2-Methoxyethyl)(methyl)amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 71061416HCID 71061416, compound

Product 1

HCID 710608604-[6-Amino-5-(pyridin-4-ylcarbamoyl)-pyridin-3-yl]-2-fluoro-benzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60 mg (0.18 mmol) of 4-[6-amino-5-(pyridin-4-ylcarbamoyl)-pyridin-3-yl]-benzoic acid and 23.13 μl (0.22 mmol) of N-(methoxyethyl)methylamine are dissolved in 2 mL DMF. 102.36 mg HATU ((2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyl-uronium hexafluorophosphate) and 59.19 μL N-methylmorpholine are added to the solution. The mixture is stirred for 3 h at room temperature. The DMF is evaporated and the product is purified by chromatography.

Workup

  1. customThe DMF is evaporated
  2. customthe product is purified by chromatography

Sources & evidence

ORD record
ord-e602f8aae6cc47809f20815ce88b64a8
Source dataset
uspto-grants-2016_03
Patent number
US09273029B2

Reaction notes

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