5-(1-Allyl-1H-imidazol-2-yl)-2-bromo-4-(2,4-dichlorophenyl)-1,3-thiazole → 5-[4-(2,4-dichlorophenyl)-5-(1H-imidazol-2-yl)-1,3-thiazol-2-yl]-3,4-dihydro-1,8-naphthyridin-2(1H)-one

HRID 2282317Notes

Reaction equation

HRID 2282317 reaction equation
C([N:4]1[CH:8]=[CH:7][N:6]=[C:5]1[C:9]1[S:13][C:12](Br)=[N:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[Cl:22])C=C.C[Sn](C)(C)[C:25]1[CH:34]=[CH:33][N:32]=[C:31]2[C:26]=1[CH2:27][CH2:28][C:29](=[O:35])[NH:30]2>>[Cl:22][C:16]1[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=1[C:10]1[N:11]=[C:12]([C:25]2[CH:34]=[CH:33][N:32]=[C:31]3[C:26]=2[CH2:27][CH2:28][C:29](=[O:35])[NH:30]3)[S:13][C:9]=1[C:5]1[NH:4][CH:8]=[CH:7][N:6]=1

Participants

3

Reactant 2

HCID 580948585-(1-Allyl-1H-imidazol-2-yl)-2-bromo-4-(2,4-dichlorophenyl)-1,3-thiazoleHCID 580951545-(trimethylstannyl)-3,4-dihydro-1,8-naphthyridin-2(1H)-one

Product 1

HCID 580951645-[4-(2,4-dichlorophenyl)-5-(1H-imidazol-2-yl)-1,3-thiazol-2-yl]-3,4-dihydro-1,8-naphthyridin-2(1H)-one

Procedure

The title compound was prepared from 5-(1-Allyl-1H-imidazol-2-yl)-2-bromo-4-(2,4-dichlorophenyl)-1,3-thiazole and 5-(trimethylstannyl)-3,4-dihydro-1,8-naphthyridin-2(1H)-one using procedures analogous to those described in Example 1-C, Steps 8 and 9. LCMS: (FA) ES+ 442, 444. 1H NMR (300 MHz, d6-DMSO) δ: 12.10-11.89 (bs, 1H), 10.64 (s, 1H), 8.25 (d, J=5.28 Hz, 1H), 7.74 (d, J=1.72 Hz, 1H), 7.60-7.46 (m, 2H), 7.39 (d, J=5.29 Hz, 1H), 7.23-6.94 (m, 2H), 4.11-4.06 (m, 1H), 3.38-3.30 (m, 1H), 3.16 (d, J=5.21 Hz, 2H).

Sources & evidence

ORD record
ord-92626f8216fa47dcbb59e622af61d432
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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