Diisopropylamine → 4-cyano-N-[2-hydroxy-4-(4-methyl-6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenyl]-benzamide

HRID 1619980Notes

Reaction equation

HRID 1619980 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1)#[N:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(NC(C)C)(C)C.[NH2:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]2[CH:49]([CH3:55])[CH2:50][C:51](=[O:54])[NH:52][N:53]=2)=[CH:44][C:43]=1[OH:56]>O.CN(C=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:41][C:42]2[CH:47]=[CH:46][C:45]([C:48]3[CH:49]([CH3:55])[CH2:50][C:51](=[O:54])[NH:52][N:53]=3)=[CH:44][C:43]=2[OH:56])=[O:9])=[CH:10][CH:11]=1)#[N:2]

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 120874-Cyanobenzoic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 179934936-(4-amino-3-hydroxy-phenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one

Product 1

HCID 674626214-cyano-N-[2-hydroxy-4-(4-methyl-6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenyl]-benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

403 mg (2.74 mmol) 4-cyano-benzoic acid and 967 mg (3.01 mmol) TBTU are added to 40 ml DMF and the mixture is stirred for 30 min at RT, then 791 μl (5.47 mmol) diisopropylamine and 600 mg (2.74 mmol) 6-(4-amino-3-hydroxy-phenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one are added and the mixture is stirred overnight. The reaction mixture is mixed with water and extracted with DCM. The org. phase is again washed with water, dried on sodium sulphate and concentrated by rotary evaporation i. V. The residue is extracted with methanol, filtered off, washed with methanol and then dried in the vacuum dryer at 50° C.

Workup

  1. stirringthe mixture is stirred overnight
  2. extractionextracted with DCM
  3. washphase is again washed with water
  4. customdried on sodium sulphate
  5. concentrationconcentrated by rotary evaporation i
  6. extractionThe residue is extracted with methanol
  7. filtrationfiltered off
  8. washwashed with methanol
  9. customdried in the vacuum dryer at 50° C.

Sources & evidence

ORD record
ord-162c4102d79f466d9ffb035af7aaa214
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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