3-(Trifluoromethyl)phenyl isocyanate → Methyl {8-fluoro-2-(7-methoxy-3,4-dihydropyrazino[1,2-a]indol-2-yl)-3-[3-(tri-fluoromethyl)phenyl]-3,4-dihydroquinazolin-4-yl}acetate

HRID 1798726Notes

Reaction equation

HRID 1798726 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[CH:50]=[CH:51][C:52]2[CH:53]=[C:54]3[CH2:61][NH:60][CH2:59][CH2:58][N:55]3[C:56]=2[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:55]3[C:56]4[CH:57]=[C:49]([O:48][CH3:47])[CH:50]=[CH:51][C:52]=4[CH:53]=[C:54]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 442643367-Methoxy-1,2,3,4-tetrahydropyrazino[1,2-a]indole

Product 1

HCID 58941056Methyl {8-fluoro-2-(7-methoxy-3,4-dihydropyrazino[1,2-a]indol-2-yl)-3-[3-(tri-fluoromethyl)phenyl]-3,4-dihydroquinazolin-4-yl}acetate

Procedure

Starting with 182 mg (0.4 mmol) of the iminophosphorane from Example 12A, 134 mg (0.4 mmol) of 1-isocyanato-3-(trifluoromethyl)benzene and 81 mg (0.4 mmol) of 7-methoxy-1,2,3,4-tetrahydropyrazino[1,2-a]indole from Example 35A, the general procedure [M] gives 140 mg (62% of theory) of product.

Workup

  1. customthe general procedure [M] gives 140 mg (62% of theory) of product

Sources & evidence

ORD record
ord-fb6fbb77bf96445f86ef7f14396aa9ee
Source dataset
uspto-grants-2013_01
Patent number
US08343981B2

Reaction notes

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