2-Aminopropanol → HCID 69673872, compound

HRID 2283247Notes

Reaction equation

HRID 2283247 reaction equation
C[C:2]1[N:7]=[N:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([C:14]([OH:16])=O)[C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:56][CH:57]([CH3:60])[CH2:58][OH:59]>CN(C=O)C.O>[OH:59][CH2:58][CH:57]([NH:56][C:14]([C:4]1[C:3]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:2][N:7]=[N:6][C:5]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:16])[CH3:60]

Participants

7

Reactant 4

HCID 51262-AminopropanolHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69673498HCID 69673498, compound2×

Product 1

HCID 69673872HCID 69673872, compoundYield 53.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 3,5-diphenylpyrridazine-4-carboxylic acid (compound 6) (250 mg, 0.90 mmol) in DMF (3 mL), DIPEA (0.47 mL, 2.71 mmol), HATU (516 mg, 1.35 mmol) were sequentially added and stirred at rt. After 15 min. 2-amino-1-propanol (203 mg, 2.71 mmol) was added and the reaction mixture was stirred at rt for 12 h. The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (3×30 mL). Combined organic extract was washed with water (2×10 mL), brine (1×10 mL) and dried over anhydrous Na2SO4 and evaporated under reduced pressure to obtain the crude product N-(1-hydroxy propan-2-yl)-3,5-diphenylpyridazine-4-carboxamide (160 mg) as an off white solid.

Workup

  1. stirringthe reaction mixture was stirred at rt for 12 h
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. extractionCombined organic extract
  4. washwas washed with water (2×10 mL), brine (1×10 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f7c3b0ead8384f3ca2fc7140cf6b980e
Source dataset
uspto-grants-2015_09
Patent number
US09145372B2

Reaction notes

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