2-Methoxyethanol → HCID 66646189, compound

HRID 547497Notes

Reaction equation

HRID 547497 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[C:9]([NH:16][CH3:17])[N:8]=[C:7]2[C:18]1[CH:19]=[C:20]([NH:24][C:25](=[O:35])[C:26]2[CH:34]=[CH:33][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=2)[CH:21]=[CH:22][CH:23]=1.[CH3:36][O:37][CH2:38][CH2:39]O.O.ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.Cl>CN(C)C=O.C(OCC)(=O)C.CCCCCCC.O.C(N(CC)CC)C>[CH3:36][O:37][CH2:38][CH2:39][O:31][C:30](=[O:32])[C:29]1[CH:33]=[CH:34][C:26]([C:25]([NH:24][C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([C:7]3[C:6]4[C:11](=[CH:12][C:13]([O:14][CH3:15])=[C:4]([O:3][CH3:2])[CH:5]=4)[N:10]=[C:9]([NH:16][CH3:17])[N:8]=3)[CH:19]=2)=[O:35])=[CH:27][CH:28]=1

Participants

9

Reactant 4

HCID 80192-MethoxyethanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 25002289HCID 25002289, compound

Product 1

HCID 66646189HCID 66646189, compoundYield 70.4%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 21899848Ethylacetate heptaneSolvent

Procedure

A mixture consisting of 55 mg (0.11 mmol) of N-[3-(6,7-dimethoxy-2-methylaminoquinazolin-4-yl)phenyl]terephthalamic acid hydrochloride, 40 μL (0.51 mmol) of 2-methoxyethanol, 47 μL of triethylamine, 17 mg of 1-hydroxybenzotriazole hydrate, and 35 mg of WSC hydrochloride, was suspended in 2 mL of dimethylformamide, followed by stirring at room temperature overnight. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layer was washed with brine, and was then dried over magnesium sulfate. The residue obtained by filtration and solvent distillation under reduced pressure was subjected to silica gel column chromatography (ethyl acetate-heptane). Thereafter, a solid precipitated with ethyl acetate-hexane was collected by filtration, and was dried under aeration to yield 40 mg of the titled compound (yield: 70%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialwas then dried over magnesium sulfate
  4. customThe residue obtained by filtration and solvent distillation under reduced pressure
  5. customThereafter, a solid precipitated with ethyl acetate-hexane
  6. filtrationwas collected by filtration
  7. customwas dried under aeration

Sources & evidence

ORD record
ord-c4c1332820754ddb9b6de78a4d6a2042
Source dataset
uspto-grants-2011_05
Patent number
US07939540B2

Reaction notes

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