Methyl Isocyanate → HCID 68867688, compound

HRID 494142Notes

Reaction equation

HRID 494142 reaction equation
[NH2:1][C:2]1[C:7]2[N:8]3[CH2:22][CH2:21][N:20]([CH3:23])[C:19](=[O:24])[C:9]3=[C:10]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[C:5](=[O:25])[N:4]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[N:3]=1.[CH3:34][N:35]=[C:36]=[O:37]>ClCCCl>[CH2:12]([O:11][C:10]1[C:6]2[C:5](=[O:25])[N:4]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[N:3]=[C:2]([NH:1][C:36]([NH:35][CH3:34])=[O:37])[C:7]=2[N:8]2[CH2:22][CH2:21][N:20]([CH3:23])[C:19](=[O:24])[C:9]=12)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 68865270HCID 68865270, compound

Product 1

HCID 68867688HCID 68867688, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-amino-2-(4-fluorobenzyl)-10-benzyloxy-8-methyl-7,8-dihydropyrazino[1′,2′:1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione (75 mg, 168 μmol) and methylisocyanate (24 mg, 419 μmol) in anhydrous 1,2-dichloroethane (3 mL) was heated in a sealed tube in an oil bath at 100° C. overnight. The product mixture was concentrated under vacuum. The intermediate dicarbonimidic diamide was dissolved in methanol, treated with an aqueous solution of KOH (0.1 mL, 2 M), and stirred at room temperature for one hour, and concentrated under vacuum. The residue was partitioned between chloroform and dilute hydrochloric acid. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum to provide the title compound. ES MS M+1=505

Workup

  1. concentrationThe product mixture was concentrated under vacuum
  2. dissolutionThe intermediate dicarbonimidic diamide was dissolved in methanol
  3. additiontreated with an aqueous solution of KOH (0.1 mL, 2 M)
  4. concentrationconcentrated under vacuum
  5. customThe residue was partitioned between chloroform and dilute hydrochloric acid
  6. extractionThe organic extract
  7. washwas washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9dcbcb1adbc547f2bea9faa3beeb44c4
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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