Isopropenyl chloroformate → (3S)-6-Chloro-1-(isopropenyloxycarbonyl)-3-methyl-3,4-dihydro-1,4,5-triazanaphthalen-2(1H)-one

HRID 21532

Reaction equation

HRID 21532 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C@H:6]([CH3:13])[NH:5]2.Cl[C:15]([O:17][C:18]([CH3:20])=[CH2:19])=[O:16]>N1C=CC=CC=1>[Cl:1][C:2]1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:15]([O:17][C:18]([CH3:20])=[CH2:19])=[O:16])[C:7](=[O:12])[C@H:6]([CH3:13])[NH:5]2

Participants

4

Reactant 2

HCID 93846Isopropenyl chloroformateHCID 57066600(3S)-6-Chloro-3-methyl-3,4-dihydro-1,4,5-triazanaphthalen-2(1H)-one

Product 1

HCID 57158666(3S)-6-Chloro-1-(isopropenyloxycarbonyl)-3-methyl-3,4-dihydro-1,4,5-triazanaphthalen-2(1H)-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The compound of Example 2 (988 mg, 5.0 mmol) was dissolved in 30 ml of anhydrous pyridine. After addition of 0.6 ml (5.5 mmol) of isopropenyl chloroformate, the mixture was stirred at room temperature for 4 h and subsequently concentrated. The residue was dissolved in ethyl acetate and washed three times with water, dried (sodium sulfate) and concentrated. After chromatography on silica gel (ethyl acetate/heptane=1:2), the desired compound was isolated and crystallized from diethyl ether/pentane; yield 380 mg (27%) of melting point 86°-87° C.

Workup

  1. concentrationsubsequently concentrated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed three times with water
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6d6ed009073d40378300b3f99b4e6525
Source dataset
uspto-grants-1995_06
Patent number
US05424311

Linked notes

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