Acetyl chloride → HCID 21106504, compound

HRID 1783686Notes

Reaction equation

HRID 1783686 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[N:17]=[C:16]([NH:18][C:19]3[CH:23]=[C:22]([CH3:24])[NH:21][N:20]=3)[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:25])=[CH:4][CH:3]=1.[C:26](Cl)(=[O:28])[CH3:27]>N1C=CC=CC=1>[CH3:24][C:22]1[NH:21][N:20]=[C:19]([NH:18][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:25])[N:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:26](=[O:28])[CH3:27])=[CH:3][CH:4]=3)[N:17]=2)[CH:23]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 11638530HCID 11638530, compound

Product 1

HCID 21106504HCID 21106504, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-(4-Amino-phenyl)-4-(5-methyl-1H-pyrazol-3-ylamino)-2H-phthalazin-1-one (C-2, 0.050 g, 0.15 mmol) was dissolved in pyridine (1 ml) at 0° C. Acetylchloride (0.024 ml, 0.33 mmol) was added and stirring was continued for 30 min at 0° C. before the mixture was allowed to warm to RT. The solvent was evaporated after 2 h stirring at RT. The residue was diluted in MeOH (1 ml) and treated with conc. NH3 (1 ml). The title compound was obtained after stirring at RT for 24 h and evaporation of the solvents in vacuum (0.016 g, 29%). 1H-NMR: (400 MHz, D6-DMSO) 11.93 (1H, s), 10.08 (1H, s), 9.26 (1H, s), 8.49 (1H, d), 8.36 (1H, d), 7.88-7.98 (2H, m), 7.61-7.69 (4H, m), 6.24 (1H, s), 2.19 (3H, s), 2.08 (3H, s); MS (API+)=375 (M+H)+.

Workup

  1. customThe solvent was evaporated after 2 h
  2. stirringstirring at RT
  3. additionThe residue was diluted in MeOH (1 ml)
  4. additiontreated with conc. NH3 (1 ml)

Sources & evidence

ORD record
ord-b07406afbca042008efd59721c0618fa
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

Loading…