Acetyl chloride → HCID 21106504, compound

HRID 1765372Notes

Reaction equation

HRID 1765372 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 room temperature. The solvent was evaporated after 2 h stirring at room temperature. The residue was diluted in MeOH (1 ml) and treated with conc. NH3 (1 ml). The title compound was obtained after stirring at room temperature 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 room temperature
  3. additionThe residue was diluted in MeOH (1 ml)
  4. additiontreated with conc. NH3 (1 ml)

Sources & evidence

ORD record
ord-05ec00c9be9c4ab5bc3f91179a9b03bf
Source dataset
uspto-grants-2007_06
Patent number
US07226923B2

Reaction notes

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