3-(Trifluoromethyl)phenyl isocyanate → Methyl {8-fluoro-2-(9-methoxy-3,4-dihydropyrazino[1,2-a]indol-2-yl)-3-[3-(trifluoromethyl)phenyl]-3,4-dihydroquinazolin-4-yl}acetate

HRID 1798725Notes

Reaction equation

HRID 1798725 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]=[CH:41][CH:40]=[C:39]([C:43]([F:46])([F:45])[F:44])[CH:38]=1)=[C:35]=O.[CH3:47][O:48][C:49]1[C:50]2[CH:51]=[C:52]3[CH2:61][NH:60][CH2:59][CH2:58][N:53]3[C:54]=2[CH:55]=[CH:56][CH:57]=1>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[N:14]=[C:35]([N:60]1[CH2:59][CH2:58][N:53]3[C:54]4[CH:55]=[CH:56][CH:57]=[C:49]([O:48][CH3:47])[C:50]=4[CH:51]=[C:52]3[CH2:61]1)[N:34]([C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([C:43]([F:46])([F:45])[F:44])[CH:38]=1)[CH:8]2[CH2:9][C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 3

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 11983908Methyl (2E)-3-{3-fluoro-2-[(triphenylphosphoranylidene)amino]phenyl}propenoateHCID 589410739-Methoxy-1,2,3,4-tetrahydropyrazino[1,2-a]indole

Product 1

HCID 58941062Methyl {8-fluoro-2-(9-methoxy-3,4-dihydropyrazino[1,2-a]indol-2-yl)-3-[3-(trifluoromethyl)phenyl]-3,4-dihydroquinazolin-4-yl}acetate

Procedure

Starting with 281 mg (0.6 mmol) of the iminophosphorane from Example 12A, 134 mg (0.6 mmol) of 1-isocyanato-3-(trifluoromethyl)benzene and 129 mg (0.6 mmol) of 9-methoxy-1,2,3,4-tetrahydropyrazino[1,2-a]indole from Example 34A, the general procedure [M] gives 239 mg (66% of theory) of product.

Workup

  1. customthe general procedure [M] gives 239 mg (66% of theory) of product

Sources & evidence

ORD record
ord-3ca3dee6976c43acb298f3d3e54607c5
Source dataset
uspto-grants-2013_01
Patent number
US08343981B2

Reaction notes

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