(2-Methoxyethyl)(methyl)amine → HCID 46869089, compound

HRID 1912474Notes

Reaction equation

HRID 1912474 reaction equation
Cl[C:2]1[C:7]2[N:8]=[C:9]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[N:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=3)[C:6]=2[N:5]=[C:4]([C:25]([OH:27])=[O:26])[CH:3]=1.[CH3:28][O:29][CH2:30][CH2:31][NH:32][CH3:33]>CCN(C(C)C)C(C)C.O>[OH:18][C:14]1[CH:13]=[C:12]([C:11]2[C:6]3[N:5]=[C:4]([C:25]([OH:27])=[O:26])[CH:3]=[C:2]([N:32]([CH2:31][CH2:30][O:29][CH3:28])[CH3:33])[C:7]=3[N:8]=[C:9]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[N:10]=2)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 300977(2-Methoxyethyl)(methyl)amineHCID 46869088HCID 46869088, compound

Product 1

HCID 46869089HCID 46869089, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 81531DiisopropylethylamineSolvent

Procedure

A mixture of Example 9 (0.1 g, 0.25 mmol) and N-(2-methoxyethyl)methyl amine (34 mg, 0.38 mmol) in DIEA (1 mL) and water (0.5 mL) was stirred at 170° C. for 2 hours. The two phases were separated and the aqueous layer concentrated in vacuo. Purification by column chromatography (increasing amount of MeOH in DCM) followed by washing with Et2O afforded the title compound as a yellow solid.

Workup

  1. customThe two phases were separated
  2. concentrationthe aqueous layer concentrated in vacuo
  3. customPurification
  4. temperatureby column chromatography (increasing amount of MeOH in DCM)
  5. washby washing with Et2O

Sources & evidence

ORD record
ord-11cfcd20c6684292b20d8627ca35fc0a
Source dataset
uspto-grants-2013_12
Patent number
US08609666B2

Reaction notes

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