Hydrochloric Acid → HCID 21701590, compound

HRID 1596292Notes

Reaction equation

HRID 1596292 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[Br:13][C:14]1[CH:33]=[CH:32][C:17]([NH:18][C:19]2[C:28]3[C:23](=[CH:24][C:25]([OH:31])=[C:26]([O:29][CH3:30])[CH:27]=3)[N:22]=[CH:21][N:20]=2)=[C:16]([F:34])[CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:55][CH2:56][N:57]1[CH2:62][CH2:61][O:60][CH2:59][CH2:58]1.[ClH:63]>C(Cl)Cl.C(Cl)Cl.CO>[ClH:63].[Br:13][C:14]1[CH:33]=[CH:32][C:17]([NH:18][C:19]2[C:28]3[C:23](=[CH:24][C:25]([O:31][CH2:55][CH2:56][N:57]4[CH2:62][CH2:61][O:60][CH2:59][CH2:58]4)=[C:26]([O:29][CH3:30])[CH:27]=3)[N:22]=[CH:21][N:20]=2)=[C:16]([F:34])[CH:15]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1355038524-[(4-Bromo-2-fluorophenyl)amino]-6-methoxy-7-quinazolinol

Product 1

HCID 21701590HCID 21701590, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Diethyl azodicarboxylate (209 mg, 1.2 mmol) was added dropwise to a suspension of 4-(4-bromo-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (146 mg, 0.4 mmol), (prepared as described for the starting material in Example 24), triphenylphosphine (314 mg, 1.2 mmol) and 4-(2-hydroxyethyl)morpholine (79 mg, 0.6 mmol) in methylene chloride (5 ml). The mixture was stirred for 1 hour at ambient temperature and purified by column flash chromatography eluting with methylene chloride/methanol (95/5 followed by 90/10) to give a white solid. The solid was dissolved in methylene chloride/methanol and 2M ethereal hydrogen chloride (0.5 ml) was added. The mixture was concentrated by evaporation and the resulting precipitate was collected by filtration, washed with ether and dried under vacuum to give 4-(4-bromo-2-fluoroanilino)-6-methoxy-7-(2-morpholinoethoxy)quinazoline hydrochloride (155 mg, 70%).

Workup

  1. custom(prepared
  2. custompurified by column flash chromatography
  3. washeluting with methylene chloride/methanol (95/5 followed by 90/10)
  4. customto give a white solid
  5. concentrationThe mixture was concentrated by evaporation
  6. filtrationthe resulting precipitate was collected by filtration
  7. washwashed with ether
  8. customdried under vacuum

Sources & evidence

ORD record
ord-50d2e21f8b564fdfab20579304b0efed
Source dataset
uspto-grants-2001_09
Patent number
US06291455B1

Reaction notes

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