Ethanolamine → HCID 178433179, compound

HRID 1922019Notes

Reaction equation

HRID 1922019 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-b624b0935f6c4901a81faef72996e5ad
Source dataset
uspto-grants-2012_05
Patent number
US08173805B2

Reaction notes

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