Methyl (2E)-3-{3-fluoro-2-[(triphenylphosphoranylidene)amino]phenyl}propenoate → Methyl {8-fluoro-2-[4-(4-fluoro-3-methylphenyl)-1-piperazinyl]-3-[6-methoxy-3-(trifluoromethyl)phenyl]-3,4-dihydro-4-quinazolinyl}acetate

HRID 459816Notes

Reaction equation

HRID 459816 reaction equation
[F:1][C:2]1[C:3]([N:14]=P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[C:4](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][CH:7]=1.[N:34]([C:37]1[CH:42]=[C:41]([C:43]([F:46])([F:45])[F:44])[CH:40]=[CH:39][C:38]=1[O:47][CH3:48])=[C:35]=O.[F:49][C:50]1[CH:55]=[CH:54][C:53]([N:56]2[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]2)=[CH:52][C:51]=1[CH3:62]>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[N:14]=[C:35]([N:59]1[CH2:58][CH2:57][N:56]([C:53]3[CH:54]=[CH:55][C:50]([F:49])=[C:51]([CH3:62])[CH:52]=3)[CH2:61][CH2:60]1)[N:34]([C:37]1[C:38]([O:47][CH3:48])=[CH:39][CH:40]=[C:41]([C:43]([F:46])([F:45])[F:44])[CH:42]=1)[CH:8]2[CH2:9][C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 3

HCID 11983908Methyl (2E)-3-{3-fluoro-2-[(triphenylphosphoranylidene)amino]phenyl}propenoateHCID 11983909Benzene, 2-isocyanato-1-methoxy-4-(trifluoromethyl)-HCID 199114471-(4-Fluoro-3-methylphenyl)piperazine

Product 1

HCID 58824019Methyl {8-fluoro-2-[4-(4-fluoro-3-methylphenyl)-1-piperazinyl]-3-[6-methoxy-3-(trifluoromethyl)phenyl]-3,4-dihydro-4-quinazolinyl}acetate

Procedure

Starting with 1.0 g (2.2 mmol) of the iminophosphorane from Example 10A, 500 mg (2.31 mmol) of 2-isocyanato-1-methoxy-4-(trifluoromethyl)benzene (Example 17A) and 427 mg (2.2 mmol) of the phenylpiperazine from Example 13A, 1.03 g (79% of theory) of crude product are obtained following filtration through silica gel (cyclohexane/ethyl acetate 2:1 (v/v)). This product is reacted further without further purification.

Workup

  1. customare obtained
  2. filtrationfiltration through silica gel (cyclohexane/ethyl acetate 2:1 (v/v))
  3. customThis product is reacted further without further purification

Sources & evidence

ORD record
ord-73a01880e3f44129ad25917309d80e5d
Source dataset
uspto-grants-2007_03
Patent number
US07196086B2

Reaction notes

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