Methanol → HCID 58669768, compound

HRID 2375429Notes

Reaction equation

HRID 2375429 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]([CH3:19])=[C:17]3[C:12]([C:13]([NH:21][CH3:22])=N[N:15]=[C:16]3[CH3:20])=[C:11]2[CH3:23])=[CH:6][CH:5]=1)[CH3:2].CNN.C[OH:28]>CC(O)=O>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]([CH3:19])=[C:17]3[C:12]([C:13](=[O:28])[N:21]([CH3:22])[N:15]=[C:16]3[CH3:20])=[C:11]2[CH3:23])=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 6061MethylhydrazineHCID 10380703HCID 10380703, compound

Product 1

HCID 58669768HCID 58669768, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Conditions

Temperature
70 °C

Procedure

A solution of ethyl-4-acetyl-1-(4-ethoxyphenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate (prepared as in EXAMPLE 85) (70 mg, 0.20 mmol) and MeOH (5 mL) in a resealable reaction vessel was mixed with methylhydrazine (0.032 mL, 0.60 mmol) and AcOH (˜3 drops). The vessel was sealed and heated at 70° C. for 12 h. The resulting slurry was allowed to cool to rt and poured into ice water (50 mL). The resulting white solid was filtered and dried under vacuum for 8 h to give 6-(4-ethoxyphenyl)-2,4,5,7-tetramethyl-2,6-dihydro-1H-pyrrolo[3,4-d]pyridazin-1-one: 1H NMR (CDCl3, 500 MHz) δ 7.00-7.26 (m, 4H), 4.10 (q, 2H), 3.71 (s, 3H), 2.49 (s, 3H), 2.45 (s, 3H), 2.30 (s, 3H), 1.48 (t, 3H); MS (ESI) 312 (M+H)+.

Workup

  1. customThe vessel was sealed
  2. temperatureto cool to rt
  3. filtrationThe resulting white solid was filtered
  4. customdried under vacuum for 8 h

Sources & evidence

ORD record
ord-2f37034eda97416eb09b504902bf9ced
Source dataset
uspto-grants-2008_12
Patent number
US07465730B2

Reaction notes

Loading…