Diisopropylethylamine → 5-Bromo-4-methyl-2-[(phenylmethyl)oxy]-N-4-pyridazinyl benzamide

HRID 2204731Notes

Reaction equation

HRID 2204731 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH2:7])=[CH:3][N:2]=1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Br:41][C:42]1[C:43]([CH3:59])=[CH:44][C:45]([O:51][CH2:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)=[C:46]([CH:50]=1)[C:47](O)=[O:48]>CN(C)C=O>[Br:41][C:42]1[C:43]([CH3:59])=[CH:44][C:45]([O:51][CH2:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)=[C:46]([CH:50]=1)[C:47]([NH:7][C:4]1[CH:5]=[CH:6][N:1]=[N:2][CH:3]=1)=[O:48]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2984924-AminopyridazineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 666112185-Bromo-4-methyl-2-[(phenylmethyl)oxy]benzoic acid

Product 1

HCID 666117865-Bromo-4-methyl-2-[(phenylmethyl)oxy]-N-4-pyridazinyl benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Pyridazinamine (207 mg, 2.18 mmol), diisopropylethylamine (0.52 ml, 2.97 mmol) and HATU (904 mg, 2.38 mmol) were added to a solution of 5-bromo-4-methyl-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 9; 636 mg, 1.98 mmol) in N,N-dimethylformamide (10 ml). The mixture was stirred for 2 hours, after 10 minutes a solid had crashed out of solution. The solid was filtered and washed with ethyl acetate (10 ml) to yield the title compound. 475 mg.

Workup

  1. filtrationThe solid was filtered
  2. washwashed with ethyl acetate (10 ml)

Sources & evidence

ORD record
ord-f57f22d7bf5d4fe48454b4deb5aeed5f
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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