Triphenylphosphine → HCID 22625042, compound

HRID 1384596Notes

Reaction equation

HRID 1384596 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[Cl: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[CH:61]=[CH:60][N:59]=[C:58]1[CH3:62]>C(Cl)Cl.CCOCC>[ClH:13].[Cl: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[CH:61]=[CH:60][N:59]=[C:58]4[CH3:62])=[C:26]([O:29][CH3:30])[CH:27]=3)[N:22]=[CH:21][N:20]=2)=[C:16]([F:34])[CH:15]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 741692-Methyl-1H-imidazole-1-ethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1355137204-(4-Chloro-2-fluorophenylamino)-7-hydroxy-6-methoxyquinazoline

Product 1

HCID 22625042HCID 22625042, compoundYield 155.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Diethyl azodicarboxylate (261 mg, 1.5 mmol) was added dropwise to a suspension of 4-(4-chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (160 mg, 0.5 mmol), (prepared as described for the starting material in Example 24), triphenylphosphine (393 mg, 1.5 mmol) and 1-(2-hydroxyethyl)-2-methylimidazole (88 mg, 0.7 mmol), (Chem.Abs. 1964, 60, 2949), in methylene chloride (8 ml) and the mixture stirred for 2 hours at ambient temperature. The mixture was diluted with ether (8 ml) and the solid product was collected by filtration. The solid was dissolved in methylene chloride/methanol and a solution of 3M ethereal hydrogen chloride (0.5 ml)was added. The resulting precipitate was collected by filtration, washed with ether and dried under vacuum to give 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(2-(2-methylimidazol-1-yl)ethoxy)quinazoline hydrochloride (180 mg, 72%). 1H NMR Spectrum: (DMSOd6; CF3COOD) 2.79(s, 3H); 4.02(s, 3H); 4.59(t, 2H); 4.72(t, 2H); 7.40(s, 1H); 7.45(d, 1H); 7.60(s, 1H); 7.62(t, 1H); 7.67(dd, 1H); 7.71(s, 1H); 8.23(s, 1H); 8.89(s, 1H) MS-ESI: 428 [MH]+

Workup

  1. custom(prepared
  2. filtrationthe solid product was collected by filtration
  3. dissolutionThe solid was dissolved in methylene chloride/methanol
  4. additiona solution of 3M ethereal hydrogen chloride (0.5 ml)was added
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-06c11465f151491195ad513436b78a80
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

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