Diazomethane → HCID 60123145, compound

HRID 2415697Notes

Reaction equation

HRID 2415697 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:19](=[O:20])[N:11]3[CH2:12][CH2:13][CH2:14][CH:15]([C:16]([OH:18])=[O:17])[N:10]3[C:9]=2[C:21]2[CH:26]=[CH:25][N:24]=[C:23]([S:27][CH3:28])[N:22]=2)=[CH:4][CH:3]=1.[N+](=[CH2:31])=[N-]>C(OCC)C.C(OCC)(=O)C.C(OCC)C>[CH3:31][O:17][C:16]([C@@H:15]1[CH2:14][CH2:13][CH2:12][N:11]2[C:19](=[O:20])[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[C:9]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([S:27][CH3:28])[N:22]=3)[N:10]12)=[O:18]

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 22636401HCID 22636401, compound

Product 1

HCID 60123145HCID 60123145, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21584169Diethylether ethylacetateSolvent

Procedure

To a solution of 2-(4-fluorophenyl)-3-(2-methylsulfanylpyrimidin-4-yl)-1-oxo-5,6,7,8-tetrahydro-1H-pyrazolo[1,2-a]pyridazine-5-carboxylic acid, 30, in diethyl ether/ethyl acetate (2.5:1, 7o mL) is added freshly generated diazomethane in diethyl ether (5 mL). The reaction is stirred for 5 minutes then quenched by the addition of HOAc (0.5 mL). The resulting solution is washed with NaHCO3, brine, dried, and concentrated in vacuo to afford 1 g (98% yield) of the desired product as a light yellow solid.

Workup

  1. customthen quenched by the addition of HOAc (0.5 mL)
  2. washThe resulting solution is washed with NaHCO3, brine
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8b536f4fcefe4fd689b975282d7079f7
Source dataset
uspto-grants-2004_11
Patent number
US06821971B2

Reaction notes

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