Methylamine → FG-7142

HRID 1085435Notes

Reaction equation

HRID 1085435 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[C:3]([C:14]([OH:16])=O)[N:2]=1.ClC(OCC)=O.[CH3:23][NH2:24]>O1CCCC1.C(N(CC)CC)C>[CH3:23][NH:24][C:14]([C:3]1[N:2]=[CH:1][C:13]2[NH:12][C:11]3[C:6]([C:5]=2[CH:4]=1)=[CH:7][CH:8]=[CH:9][CH:10]=3)=[O:16]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 10928Ethyl chloroformateHCID 1732629H-Pyrido(3,4-b)indole-3-carboxylic acid

Product 1

HCID 4375FG-7142

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

A suspension of 5 g of β-carbolin-3-carboxylic acid in a mixture of 900 ml of tetrahydrofuran and 3.6 ml of triethylamine is boiled under reflux for 15 minutes and cooled to room temperature. Freshly distilled ethyl chloroformate (2.5 ml), dissolved in 100 ml of tetrahydrofuran, is added dropwise with stirring over a period of 11/2 hours. After the reaction mixture has been stirred for an additional 30 minutes, a large excess of methylamine is added. Stirring is continued for one hour, whereafter the mixture is filtered and concentrated to approximately 50 ml under reduced pressure. Addition of water (250 ml) causes the amide to precipitate. The mixture is left at 5° C. overnight, filtered and dried at 60° C. for 15 hours. β-carbolin-3-carboxylic acid methylamide thus formed (4.1 g; 77%) is recrystallized from toluene. The melting point is 275° C.

Workup

  1. temperatureunder reflux for 15 minutes
  2. additionis added dropwise
  3. stirringStirring
  4. waitis continued for one hour, whereafter the mixture
  5. filtrationis filtered
  6. concentrationconcentrated to approximately 50 ml under reduced pressure
  7. additionAddition of water (250 ml)
  8. customto precipitate
  9. waitThe mixture is left at 5° C. overnight
  10. filtrationfiltered
  11. customdried at 60° C. for 15 hours

Sources & evidence

ORD record
ord-d6ccd2c1bf2747abac4ddffef8dfbb78
Source dataset
uspto-grants-1991_04
Patent number
US05010077

Reaction notes

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