Ethanolamine → HCID 58527396, compound

HRID 1912475Notes

Reaction equation

HRID 1912475 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.[NH2:28][CH2:29][CH2:30][OH:31]>CCN(C(C)C)C(C)C.O>[OH:31][CH2:30][CH2:29][NH:28][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

Participants

5

Reactant 2

HCID 700EthanolamineHCID 46869088HCID 46869088, compound

Product 1

HCID 58527396HCID 58527396, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 81531DiisopropylethylamineSolvent

Procedure

A mixture of Example 9 (0.1 g, 0.25 mmol) and 2-amino ethanol (24 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-16dbbf7e76664692be8b2eb01ef5b508
Source dataset
uspto-grants-2013_12
Patent number
US08609666B2

Reaction notes

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