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Sodium Carbonate → HCID 58447855, compound

HRID 1036213
Notes
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Reaction equation

HRID 1036213 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[CH:9][C:10]([NH2:13])=[N:11][CH:12]=2)=[CH:3][N:2]=1.[CH3:14][C:15]1[CH:16]=[C:17]([CH2:27][C:28](O)=[O:29])[CH:18]=[CH:19][C:20]=1[C:21]1[CH:26]=[CH:25][N:24]=[N:23][CH:22]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH3:14][C:15]1[CH:16]=[C:17]([CH2:27][C:28]([NH:13][C:10]2[CH:9]=[CH:8][C:7]([C:4]3[CH:5]=[CH:6][N:1]=[N:2][CH:3]=3)=[CH:12][N:11]=2)=[O:29])[CH:18]=[CH:19][C:20]=1[C:21]1[CH:26]=[CH:25][N:24]=[N:23][CH:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57821650HCID 57821650, compoundHCID 58447649HCID 58447649, compound

Product 1

HCID 58447855
HCID 58447855, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-(pyridazin-4-yl)pyridin-2-amine 134-1 (53 mg, 0.31 mmol), 2-(3-methyl-4-(pyridazin-4-yl)phenyl)acetic acid 134-3 (73 mg, 0.32 mmol), HATU (122 mg, 0.32 mmol) and DIEA (80 uL, 0.46 mmol) in DMF (1.0 ml) was stirred at room temperature overnight. Then it was distributed between ethyl acetate (40 ml) and 3% Na2CO3 aqueous solution (40 ml) and extracted with 0.5 N HCl solution (30 ml). The aqueous extraction was treated with Na2CO3 to adjust the pH to around 10 followed by extraction with ethyl acetate (30 ml×2). The combined organic extractions were dried over Na2SO4 and concentrated by evaporation. The residue was subjected to reverse phase HPLC to yield 2-(3-methyl-4-(pyridazin-4-yl)phenyl)-N-(5-(pyridazin-4-yl)pyridin-2-yl)acetamide 134 as off white solid. MS m/z 383.2 (M+1).

Workup

  1. extractionextracted with 0.5 N HCl solution (30 ml)
  2. extractionThe aqueous extraction
  3. additionwas treated with Na2CO3
  4. extractionfollowed by extraction with ethyl acetate (30 ml×2)
  5. extractionThe combined organic extractions
  6. dry with materialwere dried over Na2SO4
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-5984a87b68904b7bbfecdef5cbc30d0f
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08546396B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes