Water → 2-tert-Butoxycarbonylmethyl-4-(3-chloro-4-methoxybenzyl)amino-6-cyano-1(2H)-phthalazinone

HRID 324347Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[CH2:5][NH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=2)[C:10](=[O:19])[NH:9][N:8]=1.Br[CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].C(=O)([O-])[O-].[K+].[K+].O>CN1CCCC1=O>[C:30]([O:29][C:27]([CH2:26][N:9]1[N:8]=[C:7]([NH:6][CH2:5][C:4]2[CH:20]=[CH:21][C:22]([O:23][CH3:24])=[C:2]([Cl:1])[CH:3]=2)[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=2)[C:10]1=[O:19])=[O:28])([CH3:33])([CH3:32])[CH3:31]

Participants

Conditions

Temperature: 80 °C

Procedure

4-(3-Chloro-4-methoxybenzyl)amino-6-cyanol-1(2H)-phthalazinone (0.20 g) prepared in Example 21 was dissolved in 5 ml of N-methyl-2-pyrrolidinone, followed by the addition of 0.14 g of t-butyl bromoacetate and 0.24 g of potassium carbonate. The obtained mixture was stirred at 80° C. for 4 hours and poured into water, followed by extraction with ethyl acetate. The organic phase was washed with water twice and with a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and freed from the solvent by vacuum distillation. The title compound (0.41 g) was obtained as a yellow crystal.

Workup

extractionfollowed by extraction with ethyl acetate
washThe organic phase was washed with water twice
dry with materialwith a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate
distillationfreed from the solvent by vacuum distillation

Sources & evidence

ORD record: ord-a4f227f2de6844ed8b80d6f56d138f20
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06218392B1

Reaction notes

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