(2-Methoxyethyl)(methyl)amine → HCID 67315193, compound

HRID 1011365Notes

Reaction equation

HRID 1011365 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[C:12]1[C:20]2[C:15](=[N:16][C:17]([CH:21]=[CH2:22])=[CH:18][CH:19]=2)[CH2:14][O:13]1.[CH3:23][O:24][CH2:25][CH2:26][NH:27][CH3:28]>C(N(CC)CC)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[C:12]1[C:20]2[C:15](=[N:16][C:17]([CH2:21][CH2:22][N:27]([CH2:26][CH2:25][O:24][CH3:23])[CH3:28])=[CH:18][CH:19]=2)[CH2:14][O:13]1

Participants

4

Reactant 2

HCID 300977(2-Methoxyethyl)(methyl)amine2×HCID 67314553HCID 67314553, compound

Product 1

HCID 67315193HCID 67315193, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineCatalyst

Conditions

Temperature
100 °C

Procedure

Following the method described in Example 19, 5-fluoro-3-(2-vinyl-7H-furo[3,4-b]pyridin-5-ylidene)-1,3-dihydro-indol-2-one (80 mg, 0.27 mmol) and (2-methoxyethyl)methylamine (450 mg, 5.04 mmol) are heated 100° C. for 2 h. Additional (2-methoxyethyl)methylamine is added and heating is continued for 1 hr. The reaction mixture is cooled and treated with triethylamine (10 drops). The reaction mixture is loaded onto silica gel and purified by chromatography (silica gel, MeOH-Chloroform). The product containing fractions are concentrated and triturated with EtOAc-hexane. The solid obtained is collected by filtration and dried to provide the title compound (55 mg, 53%) as a yellow solid.

Workup

  1. temperatureheating
  2. temperatureThe reaction mixture is cooled
  3. custompurified by chromatography (silica gel, MeOH-Chloroform)
  4. additionThe product containing fractions
  5. concentrationare concentrated
  6. customtriturated with EtOAc-hexane
  7. customThe solid obtained
  8. filtrationis collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-79aed26946834e1da81f72869194125a
Source dataset
uspto-grants-2011_07
Patent number
US07977351B2

Reaction notes

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