Diisopropylethylamine → HCID 67107764, compound

HRID 1623818Notes

Reaction equation

HRID 1623818 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH2:7])=[CH:3][N:2]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[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])=[C:55]([F:60])[CH:54]=2)=[C:46]([CH:50]=1)[C:47](O)=[O:48]>CN(C)C=O.C(OCC)(=O)C>[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])=[C:55]([F:60])[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

7

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 67107253HCID 67107253, compound

Product 1

HCID 67107764HCID 67107764, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Pyridazinamine (0.42 g, 4.37 mmol), HATU (2.22 g, 5.83 mmol) and diisopropylethylamine (1.53 ml, 8.74 mmol) were added to a solution of 5-bromo-2-{[(3,4-difluorophenyl)methyl]oxy}benzoic acid (may be prepared by Description 89; 1 g, 2.91 mmol) in N,N-dimethylformamide (25 ml). The mixture was stirred at room temperature for 2 hours. The mixture was diluted with ethyl acetate (200 ml), shaken and allowed to stand for 5 min. The precipitate was filtered, washed with water (25 ml) and ethyl acetate (50 ml), and dried under vacuum to yield the title compound as a white solid. No further purification was carried out. 900 mg.

Workup

  1. stirringshaken
  2. waitto stand for 5 min
  3. filtrationThe precipitate was filtered
  4. washwashed with water (25 ml) and ethyl acetate (50 ml)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-ebd76041c8e847658bf08d338e11767a
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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