Methyl (2E)-3-{3-fluoro-2-[(triphenylphosphoranylidene)amino]phenyl}propenoate → Methyl [8-fluoro-3-(2-methoxy-5-trifluoromethylphenyl)-2-(9-methoxy-3,4-dihydro-1H-pyrazino[1,2-a]indol-2-yl)-3,4-dihydroquinazolin-4-yl]acetate

HRID 1798724Notes

Reaction equation

HRID 1798724 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.[CH3:49][O:50][C:51]1[C:52]2[CH:53]=[C:54]3[CH2:63][NH:62][CH2:61][CH2:60][N:55]3[C:56]=2[CH:57]=[CH:58][CH:59]=1>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[N:14]=[C:35]([N:62]1[CH2:61][CH2:60][N:55]3[C:56]4[CH:57]=[CH:58][CH:59]=[C:51]([O:50][CH3:49])[C:52]=4[CH:53]=[C:54]3[CH2:63]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])[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 589410739-Methoxy-1,2,3,4-tetrahydropyrazino[1,2-a]indole

Product 1

HCID 58941066Methyl [8-fluoro-3-(2-methoxy-5-trifluoromethylphenyl)-2-(9-methoxy-3,4-dihydro-1H-pyrazino[1,2-a]indol-2-yl)-3,4-dihydroquinazolin-4-yl]acetate

Procedure

Starting with 500 mg (1.1 mmol) of the iminophosphorane from Example 12A, 238 mg (1.1 mmol) of 2-isocyanato-1-methoxy-4-(trifluoromethyl)benzene and 222 mg (1.1 mmol) of 9-methoxy-1,2,3,4-tetrahydropyrazino[1,2-a]indole from Example 34A, the general procedure [M] gives 270 mg (38% of theory) of product.

Workup

  1. customthe general procedure [M] gives 270 mg (38% of theory) of product

Sources & evidence

ORD record
ord-b10171ec84784dff8026a53ae572f289
Source dataset
uspto-grants-2013_01
Patent number
US08343981B2

Reaction notes

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