1-(4-Fluorophenyl)piperazine → Methyl {8-fluoro-2-[4-(4-fluorophenyl)-1-piperazinyl]-3-[6-methoxy-3-chlorophenyl]-3,4-dihydro-4-quinazolinyl}acetate

HRID 459818Notes

Reaction equation

HRID 459818 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.[CH3:34][O:35][C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][C:37]=1[N:43]=[C:44]=O.[F:46][C:47]1[CH:52]=[CH:51][C:50]([N:53]2[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]2)=[CH:49][CH:48]=1>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[N:14]=[C:44]([N:56]1[CH2:55][CH2:54][N:53]([C:50]3[CH:49]=[CH:48][C:47]([F:46])=[CH:52][CH:51]=3)[CH2:58][CH2:57]1)[N:43]([C:37]1[C:36]([O:35][CH3:34])=[CH:41][CH:40]=[C:39]([Cl:42])[CH:38]=1)[CH:8]2[CH2:9][C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 3

HCID 752601-(4-Fluorophenyl)piperazineHCID 1440094-Chloro-2-isocyanato-1-methoxybenzeneHCID 11983908Methyl (2E)-3-{3-fluoro-2-[(triphenylphosphoranylidene)amino]phenyl}propenoate

Product 1

HCID 58824015Methyl {8-fluoro-2-[4-(4-fluorophenyl)-1-piperazinyl]-3-[6-methoxy-3-chlorophenyl]-3,4-dihydro-4-quinazolinyl}acetate

Procedure

Starting with 1.0 g (2.2 mmol) of the iminophosphorane from Example 10A, 423 mg (2.31 mmol) of 2-methoxy-5-chlorophenyl isocyanate and 396 mg (2.2 mmol) of 4-fluorophenylpiperazine, 621 mg (52% of theory) of product are obtained after purification by preparative HPLC.

Workup

  1. customare obtained
  2. customafter purification by preparative HPLC

Sources & evidence

ORD record
ord-8e79e24a26fd4347a943b758c2a6e265
Source dataset
uspto-grants-2007_03
Patent number
US07196086B2

Reaction notes

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