1-(4,6-Dichloro-1,5-naphthyridin-3-yl)ethan-1-one → HCID 178467146, compound

HRID 526200Notes

Reaction equation

HRID 526200 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[N:10]=2)[N:5]=[CH:4][C:3]=1[C:13](=[O:15])[CH3:14].[NH2:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([CH2:23][OH:24])[CH2:19][CH2:18]1>>[Cl:12][C:9]1[N:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][C:3]([C:13](=[O:15])[CH3:14])=[C:2]2[NH:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([CH2:23][OH:24])[CH2:19][CH2:18]1

Participants

3

Reactant 2

HCID 897049771-(4,6-Dichloro-1,5-naphthyridin-3-yl)ethan-1-oneHCID 178511560HCID 178511560, compound

Product 1

HCID 178467146HCID 178467146, compoundYield 65%

Procedure

Following general procedure I, 1-(4,6-dichloro-1,5-naphthyridin-3-yl)ethanone (200 mg, 0.83 mmol) was reacted with (trans-4-aminocyclohexyl)methanol (130 mg, 1.0 mmol) to afford the desired product (180 mg, 65%) as an orange-yellow solid: 1H NMR (500 MHz, CDCl3) δ 10.90 (s, 1H), 8.94 (s, 1H), 8.08 (d, J=8.7 Hz, 1H), 7.52 (d, J=8.7 Hz, 1H), 5.10-4.92 (m, 1H), 3.58-3.47 (m, 2H), 2.68 (s, 3H), 2.37-2.23 (m, 2H), 2.01-1.89 (m, 2H), 1.65-1.51 (m, 1H), 1.42-1.30 (m, 2H), 1.29-1.18 (m, 2H); ESI MS m/z 334 [M+H]+

Sources & evidence

ORD record
ord-957103f4cbf5439f98de2bc603d0ecf9
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

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