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Diisopropylethylamine → 5-Bromo-2-{[(4-fluorophenyl)methyl]oxy}-N-4-pyridazinylbenzamide

HRID 1623817
Notes
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Reaction equation

HRID 1623817 reaction equation
C(N(C(C)C)CC)(C)C.[N:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][N:11]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Br:41][C:42]1[CH:43]=[CH:44][C:45]([O:51][CH2:52][C:53]2[CH:58]=[CH:57][C:56]([F:59])=[CH:55][CH:54]=2)=[C:46]([CH:50]=1)[C:47](O)=[O:48]>CN(C)C=O>[Br:41][C:42]1[CH:43]=[CH:44][C:45]([O:51][CH2:52][C:53]2[CH:58]=[CH:57][C:56]([F:59])=[CH:55][CH:54]=2)=[C:46]([CH:50]=1)[C:47]([NH:16][C:13]1[CH:14]=[CH:15][N:10]=[N:11][CH:12]=1)=[O:48]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2984924-AminopyridazineHCID 87068895-Bromo-2-[(4-fluorobenzyl)oxy]benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 671073585-Bromo-2-{[(4-fluorophenyl)methyl]oxy}-N-4-pyridazinylbenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Diisopropylethylamine (1.61 ml, 9.23 mmol), 4-pyridazinamine (0.53 g, 5.54 mmol) and HATU (2.63 g, 6.92 mmol) were added to a solution of 5-bromo-2-{[(4-fluorophenyl)methyl]oxy}benzoic acid (may be prepared as described in Description 87; 1.5 g, 4.61 mmol) in N,N-dimethylformamide (10 ml). The mixture was stirred for 2 hours and the solid was filtered and washed with ethyl acetate to yield the title compound as a white solid. 658 mg.

Workup

  1. filtrationthe solid was filtered
  2. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-111e43241f9c4dd1afa034082bf0d761
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08778939B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes