Dimethylformamide → (R)-5-methoxy-6-(2-phenyl-benzoxazol-6-yl)-4,5-dihydro-2H-pyridazin-3-one

HRID 1619943Notes

Reaction equation

HRID 1619943 reaction equation
[CH3:1][O:2][C@@H:3]([C:8](=O)[C:9]1[CH:23]=[CH:22][C:12]2[N:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:15][C:11]=2[CH:10]=1)[CH2:4][C:5](O)=[O:6].CN(C(O[N:33]1[N:41]=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN(C=O)C.NN>C1COCC1>[CH3:1][O:2][C@H:3]1[C:8]([C:9]2[CH:23]=[CH:22][C:12]3[N:13]=[C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[O:15][C:11]=3[CH:10]=2)=[N:41][NH:33][C:5](=[O:6])[CH2:4]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 9321HydrazineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67464500(R)-3-methoxy-4-oxo-4-(2-phenyl-benzoxazol-6-yl)-butyric acid

Product 1

HCID 67466128(R)-5-methoxy-6-(2-phenyl-benzoxazol-6-yl)-4,5-dihydro-2H-pyridazin-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

140 mg (430 μmol) (R)-3-methoxy-4-oxo-4-(2-phenyl-benzoxazol-6-yl)-butyric acid are combined at RT with 190 mg (500 μmol) HATU, 200 μl (1424 μmol) TEA and 2 ml DMF. The mixture is stirred for 10 min, then 431 μl (431 μmol) hydrazine 1M in THF are added. The mixture is stirred for a further 2 h at RT, then extracted with DCM and phosphate buffer (pH7). The org. phase is dried and evaporated down. The residue is purified by RP-HPLC.

Workup

  1. stirringThe mixture is stirred for a further 2 h at RT
  2. extractionextracted with DCM and phosphate buffer (pH7)
  3. customphase is dried
  4. customevaporated down
  5. customThe residue is purified by RP-HPLC

Sources & evidence

ORD record
ord-b142b7ed87e54f68ae81d11bd716924d
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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