Ethanolamine → HCID 178433179, compound

HRID 1510947Notes

Reaction equation

HRID 1510947 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C@@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([F:29])([F:28])[F:27])=[O:17])[CH2:12][CH2:11]2)[N:3]=1.[NH2:30][CH2:31][CH2:32][OH:33].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:33][CH2:32][CH2:31][NH:30][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C@@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([F:29])([F:28])[F:27])=[O:17])[CH2:12][CH2:11]2)[N:3]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 11430Potassium CarbonateHCID 178432891HCID 178432891, compound

Product 1

HCID 178433179HCID 178433179, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of cis-4-[(4-chloro-6-methyl-1,3,5-triazin-2-yl)amino]-N-{[2-(trifluoromethyl)phenyl]methyl}cyclohexanecarboxamide (70 mgs, 0.16 mmol, 1.0 equiv), 2-aminoethanol (15 mgs, 0.25 mmol, 1.5 equiv), and potassium carbonate (34 mgs, 0.25 mmol, 1.0 equiv) in acetonitrile (3 ml) was heated to reflux for 16 h. The solvent was removed under reduced pressure, and the residue was extracted with CH2Cl2 and washed with water. The organic layer was dried over sodium sulfate and concentrated. The residue was purified via reverse-phase HPLC purification to afford the title compound. MS (ES+): m/e 453.3 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 h
  3. customThe solvent was removed under reduced pressure
  4. extractionthe residue was extracted with CH2Cl2
  5. washwashed with water
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified via reverse-phase HPLC purification

Sources & evidence

ORD record
ord-079ad383b9fe4e7d87c0a48cc1eabc0a
Source dataset
uspto-grants-2012_07
Patent number
US08212032B2

Reaction notes

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