4-Amino-1-methylpiperidine → HCID 117773225, compound

HRID 526198Notes

Reaction equation

HRID 526198 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].[CH3:16][N:17]1[CH2:22][CH2:21][CH:20]([NH2:23])[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:23][CH:20]1[CH2:21][CH2:22][N:17]([CH3:16])[CH2:18][CH2:19]1

Participants

3

Reactant 2

HCID 27375314-Amino-1-methylpiperidineHCID 897049771-(4,6-Dichloro-1,5-naphthyridin-3-yl)ethan-1-one

Product 1

HCID 117773225HCID 117773225, compoundYield 69%

Procedure

Following general procedure I, 1-(4,6-dichloro-1,5-naphthyridin-3-yl)ethanone (220 mg, 0.91 mmol) was reacted with 1-methylpiperidin-4-amine (160 mg, 1.4 mmol) to afford the desired product (200 mg, 69%) as a light brown solid: 1H NMR (500 MHz, CDCl3) δ 10.98 (s, 1H), 8.96 (s, 1H), 8.10 (d, J=8.7 Hz, 1H), 7.53 (d, J=8.7 Hz, 1H), 5.11 (br s, 1H), 2.98-2.870 (m, 2H), 2.69 (s, 3H), 2.41-2.28 (m, 5H), 2.28-2.20 (m, 2H), 1.85-1.73 (m, 2H); ESI MS m/z 319 [M+H]+; ESI MS m/z 319 [M+H]+

Sources & evidence

ORD record
ord-318fba35a2dd472aaca1014a9bd0ef92
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

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