Methylamine → HCID 9797631, compound

HRID 2182514Notes

Reaction equation

HRID 2182514 reaction equation
[CH3:1][NH2:2].[CH2:3]([N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([C:19]2[O:20][C:21]([C:24](Cl)=[O:25])=[CH:22][CH:23]=2)=[N:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C1COCC1>[CH2:3]([N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([C:19]2[O:20][C:21]([C:24](=[O:25])[NH:2][CH3:1])=[CH:22][CH:23]=2)=[N:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 22480358HCID 22480358, compound

Product 1

HCID 9797631HCID 9797631, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

2.97 ml (5.94 mmol) of a 2 M solution of methylamine in THF were initially charged in 20 ml of THF, and a solution of 0.8 g (2.4 mmol) of 1-benzyl-3-(5-chlorocarbonyl-2-furyl)indazole in 10 ml of THF was added dropwise at RT. After 1 h, the mixture was poured into ice-water and the oil that separated off was extracted with ethyl acetate. The organic phase was washed with 1 N hydrochloric acid, dried and concentrated using a rotary evaporator. The crude product was recrystallized from isopropanol. This gave 0.44 g (55%) of the title compound.

Workup

  1. customthe oil that separated off
  2. extractionwas extracted with ethyl acetate
  3. washThe organic phase was washed with 1 N hydrochloric acid
  4. customdried
  5. concentrationconcentrated
  6. customa rotary evaporator
  7. customThe crude product was recrystallized from isopropanol

Sources & evidence

ORD record
ord-13bbc0766a8a431aa87c2aea94f1b91e
Source dataset
uspto-grants-2005_05
Patent number
US06897232B2

Reaction notes

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