Ethanolamine → HCID 10117539, compound

HRID 1062591Notes

Reaction equation

HRID 1062591 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[C:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:9][CH:10]=2)[C:5](=[O:21])[N:4]([CH2:22][C:23]2[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=2)[C:3]1=[O:32].CCN=C=NC[CH2:39][CH2:40][N:41]([CH3:43])[CH3:42].Cl.C1C=CC2N(O)N=NC=2C=1.C(CN)O>CN(C=O)C.O>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[C:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:9][CH:10]=2)[C:5](=[O:21])[N:4]([CH2:22][C:23]2[CH:31]=[CH:30][C:26]([C:27]([O:29][CH2:39][CH2:40][N:41]([CH3:43])[CH3:42])=[O:28])=[CH:25][CH:24]=2)[C:3]1=[O:32]

Participants

7

Reactant 4

HCID 700EthanolamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 102241814-((1-Methyl-2,4-dioxo-6-(3-phenylprop-1-yn-1-yl)-1,2-dihydroquinazolin-3(4H)-yl)methyl)benzoic acid

Product 1

HCID 10117539HCID 10117539, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.72 g (1.7 mmol) 4-[1-Methyl-2,4-dioxo-6-(3-phenyl-prop-1-ynyl)-1,4-dihydro-2H-quinazolin-3-ylmethyl]-benzoic acid, 0.43 g (2.2 mmol) EDAC-HCl, 0.29 g (2.2 mmol) HOBT in 10 ml DMF is treated with 0.19 g (2.2 mmol) ethanolamine. The resulting mixture is stirred overnight at room temperature before diluting with water and extracting with 1:1 EtOAc/Et2O (2×). The combined organic extracts are washed with saturated aqueous NaCl (3×), dried (MgSO4). The resulting oil is dissolved in EtOAc and treated with saturated methanolic HCl. Concentration provided a solid which is triturated in EtOAc and filtered.

Workup

  1. extractionextracting with 1:1 EtOAc/Et2O (2×)
  2. washThe combined organic extracts are washed with saturated aqueous NaCl (3×)
  3. dry with materialdried (MgSO4)
  4. dissolutionThe resulting oil is dissolved in EtOAc
  5. additiontreated with saturated methanolic HCl
  6. concentrationConcentration
  7. customprovided a solid which
  8. customis triturated in EtOAc
  9. filtrationfiltered

Sources & evidence

ORD record
ord-6545b044a11c4b3387ceef92a2049efb
Source dataset
uspto-grants-2005_11
Patent number
US06962922B2

Reaction notes

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