Dimethylformamide → Pazinaclone

HRID 2309393Notes

Reaction equation

HRID 2309393 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[C:20](=[O:21])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:13]3[CH2:22][C:23](O)=[O:24])=[N:9]2)=[CH:4][CH:3]=1.CN(C)C=O.[O:31]1[C:35]2([CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)[O:34][CH2:33][CH2:32]1.P(C#N)(=O)(OCC)OCC>O.C(N(CC)CC)C>[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[CH:13]([CH2:22][C:23]([N:38]4[CH2:39][CH2:40][C:35]5([O:34][CH2:33][CH2:32][O:31]5)[CH2:36][CH2:37]4)=[O:24])[C:14]4[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=4)[C:20]3=[O:21])=[N:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 76257Diethyl cyanophosphonateHCID 13655948HCID 13655948, compound

Product 1

HCID 59743PazinacloneYield 98.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 20.4 g of 2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxoisoindoline-1-acetic acid and 250 ml of dimethylformamide were added 16 ml of triethylamine, 10.4 g of 1,4-dioxa-8-azaspiro[4.5]decane and 16 ml of diethyl phosphorocyanidate, and the mixture was stirred for 20 minutes. After addition of water, the resulting crystalline precipitate was collected by filtration, washed with water and dried to give 26.4 g of crude crystals. Recrystallization from methylene chloride-ethyl acetate gave 27.1 g of colorless crystals melting at 238°-239° C.

Workup

  1. filtrationthe resulting crystalline precipitate was collected by filtration
  2. washwashed with water
  3. customdried
  4. customto give 26.4 g of crude crystals
  5. customRecrystallization from methylene chloride-ethyl acetate

Sources & evidence

ORD record
ord-820da457148f4d8880bb8d35198213db
Source dataset
uspto-grants-1987_09
Patent number
US04695572

Reaction notes

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