6-Bromo-3,4-dihydro-1,8-naphthyridin-2(1H)-one → (E)-N-((1-ethyl-1H-indol-4-yl)methyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide

HRID 2097166Notes

Reaction equation

HRID 2097166 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[C:7]([CH2:12][N:13]([CH3:18])[C:14](=[O:17])[CH:15]=[CH2:16])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1)[CH3:2].CN(CC1SC2C=CC=CC=2C=1C)C(=O)C=C.Br[C:37]1[CH:38]=[C:39]2[C:44](=[N:45][CH:46]=1)[NH:43][C:42](=[O:47])[CH2:41][CH2:40]2.BrC1C=NC2NC(=O)C(C)(C)NCC=2C=1>>[CH2:1]([N:3]1[C:11]2[C:6](=[C:7]([CH2:12][N:13]([CH3:18])[C:14](=[O:17])/[CH:15]=[CH:16]/[C:37]3[CH:46]=[N:45][C:44]4[NH:43][C:42](=[O:47])[CH2:41][CH2:40][C:39]=4[CH:38]=3)[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1)[CH3:2]

Participants

5

Reactant 4

HCID 110963256-Bromo-3,4-dihydro-1,8-naphthyridin-2(1H)-oneHCID 17930139N-methyl-N-(3-methyl-benzo[b]thiophen-2-ylmethyl)acrylamideHCID 59277581HCID 59277581, compoundHCID 594569147-Bromo-3,3-dimethyl-1,3,4,5-tetrahydropyrido[2,3-e][1,4]diazepin-2-one

Product 1

HCID 16661130(E)-N-((1-ethyl-1H-indol-4-yl)methyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamideYield 46%

Procedure

The title compound was prepared according to the procedure of Example 2, except substituting (N-((1-ethyl-1H-indol-4-yl)methyl)-N-methylacrylamide) for N-methyl-N-(3-methyl-benzo[b]thiophen-2-ylmethyl)acrylamide and 6-bromo-3,4-dihydro-1,8-naphthyridin-2(1H)-one for 7-bromo-3,3-dimethyl-1,3,4,5-tetrahydro-pyrido[2,3-e][1,4]diazepin-2-one. The title compound (329 mg, 46%) was obtained as an off-white solid and a mixture of amide rotomers: 1H NMR (400 MHz, DMSO-d6) δ 10.62-10.58 (m, 1H), 8.38-7.98 (m, 2H), 7.57-7.53 (m, 1H), 7.42-7.08 (m, 4H), 6.92-6.78 (m, 1H), 6.51 (s, 1H), 5.05-4.88 (m, 2H), 4.22-4.19 (m, 2H), 3.04-2.85 (m, 5H), 2.55-2.50 (m, 2H), 1.35 (t, J=7.2 Hz, 3H); ESI MS m/z 389 [C23H24N4O2+H]+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-e85bf8cf568f4b8980b14b57c5871ab0
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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