Methylamine → HCID 9797631, compound

HRID 1275713Notes

Reaction equation

HRID 1275713 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 2M 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 1N 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. m.p.: 182-183° C.

Workup

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

Sources & evidence

ORD record
ord-6cc6f1e4109f4f468fad001c84f0f1d7
Source dataset
uspto-grants-2000_12
Patent number
US06162819

Reaction notes

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