2-Methyl-1,2,3,4-tetrahydroquinoline → [2-(3-Chloro-4-fluoro-phenoxy)-pyridin-3-yl]-(3,4-dihydro-2H-[1,5]naphthyridin-1-yl)-methanone

HRID 1877366Notes

Reaction equation

HRID 1877366 reaction equation
ClC1C=CC(Cl)=CC=1OC1N=CC=CC=1C(O)=O.[Cl:19][C:20]1[CH:21]=[C:22]([CH:33]=[CH:34][C:35]=1[F:36])[O:23][C:24]1[N:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26]([OH:28])=O.CC1CCC2C(=CC=CC=2)N1.[NH:48]1[C:57]2[C:52](=[N:53][CH:54]=[CH:55][CH:56]=2)[CH2:51][CH2:50][CH2:49]1>>[Cl:19][C:20]1[CH:21]=[C:22]([CH:33]=[CH:34][C:35]=1[F:36])[O:23][C:24]1[C:25]([C:26]([N:53]2[C:52]3[C:57](=[N:48][CH:49]=[CH:50][CH:51]=3)[CH2:56][CH2:55][CH2:54]2)=[O:28])=[CH:29][CH:30]=[CH:31][N:32]=1

Participants

5

Reactant 4

HCID 962892-Methyl-1,2,3,4-tetrahydroquinolineHCID 69174951,2,3,4-Tetrahydro-1,5-naphthyridineHCID 128493372-(3-Chloro-4-fluoro-phenoxy)-nicotinic acidHCID 167959962-(2,5-Dichloro-phenoxy)-nicotinic acid

Product 1

HCID 59294527[2-(3-Chloro-4-fluoro-phenoxy)-pyridin-3-yl]-(3,4-dihydro-2H-[1,5]naphthyridin-1-yl)-methanone

Procedure

The title compound was prepared in analogy to Example 67 replacing 2-(2,5-dichloro-phenoxy)-nicotinic acid with 2-(3-chloro-4-fluoro-phenoxy)-nicotinic acid (Example 77, Step 1) and 2-methyl-1,2,3,4-tetrahydro-quinoline with 1,2,3,4-tetrahydro-[1,5]naphthyridine ([CAS RN 13993-61-8]). MS (ISN): 383.9 [M+H]+.

Sources & evidence

ORD record
ord-68ed5bd1d7ac4141bf7a1c0a06eb161d
Source dataset
uspto-grants-2012_11
Patent number
US08309734B2

Reaction notes

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