Diethylethanolamine → 7-(2-(N,N-diethylamino)ethoxy)-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline

HRID 1791611Notes

Reaction equation

HRID 1791611 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([N:22]([CH2:26][CH3:27])[CH2:23][CH2:24][OH:25])[CH3:21].O[C:29]1[CH:38]=[C:37]2[C:32]([C:33]([O:39][C:40]3[CH:41]=[C:42]4[C:46](=[CH:47][CH:48]=3)[NH:45][C:44]([CH3:49])=[CH:43]4)=[N:34][CH:35]=[N:36]2)=[CH:31][C:30]=1[O:50][CH3:51].N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl>[CH2:20]([N:22]([CH2:23][CH2:24][O:25][C:29]1[CH:38]=[C:37]2[C:32]([C:33]([O:39][C:40]3[CH:41]=[C:42]4[C:46](=[CH:47][CH:48]=3)[NH:45][C:44]([CH3:49])=[CH:43]4)=[N:34][CH:35]=[N:36]2)=[CH:31][C:30]=1[O:50][CH3:51])[CH2:26][CH3:27])[CH3:21]

Participants

6

Reactant 4

HCID 7497DiethylethanolamineHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1357631087-hydroxy-6-methoxy-4-(2-methyl-1H-indol-5-yloxy)quinazoline

Product 1

HCID 220305667-(2-(N,N-diethylamino)ethoxy)-6-methoxy-4-(2-methylindol-5-yloxy)quinazolineYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (262 mg, 1 mmol) and N,N-diethylethanolamine (88 mg, 0.75 mmol) were added to a suspension of 7-hydroxy-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline (160 mg, 0.5 mmol), (prepared as described in Example 49), in methylene chloride (5 ml), followed by the addition, in portions, of diethyl azodicarboxylate (165 μl, 1 mmol). After stirring for 1 hour at ambient temperature, the volatiles were removed under vacuum. The residue was purified by column chromatography eluting with methylene chloride/methanol (95/5) followed by methylene chloride/3M ammonia in methanol (90/10) to give 7-(2-(N,N-diethylamino)ethoxy)-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline (147 mg, 70%).

Workup

  1. customthe volatiles were removed under vacuum
  2. customThe residue was purified by column chromatography
  3. washeluting with methylene chloride/methanol (95/5)

Sources & evidence

ORD record
ord-3ee680b06e7f4affbf1c69d8a63a3d10
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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