3-(Dimethylamino)pyrrolidine → HCID 117773231, compound

HRID 526213Notes

Reaction equation

HRID 526213 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]([CH3:23])[CH:18]1[CH2:22][CH2:21][NH:20][CH2:19]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:10][C:11]1[CH:6]=[N:5][C:4]([N:20]2[CH2:21][CH2:22][CH:18]([N:17]([CH3:23])[CH3:16])[CH2:19]2)=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 27585193-(Dimethylamino)pyrrolidineHCID 897049771-(4,6-Dichloro-1,5-naphthyridin-3-yl)ethan-1-one

Product 1

HCID 117773231HCID 117773231, compoundYield 185%

Procedure

Following general procedure I, 1-(4,6-dichloro-1,5-naphthyridin-3-yl)ethanone (250 mg, 1.0 mmol) was reacted with N,N-dimethylpyrrolidin-3-amine (260 mg, 1.2 mmol) to afford the desired product (380 mg, 89%) as an orange solid: 1H NMR (300 MHz, CDCl3) δ 11.35 (s, 1H), 9.00 (s, 1H), 8.10 (d, J=8.7 Hz, 1H), 8.02 (dd, J=2.7, 0.7 Hz, 1H), 7.47 (d, J=8.7 Hz, 1H), 7.30 (dd, J=8.9, 2.7 Hz, 1H), 6.35 (d, J=8.9 Hz, 1H), 3.88-3.77 (m, 1H), 3.62-3.72 (m, 1H), 3.49-3.37 (m, 1H), 3.33-3.22 (m, 1H), 2.94-2.76 (m, 1H), 2.68 (s, 3H), 2.34 (s, 6H), 2.34-2.18 (m, 1H), 2.06-1.89 (m, 1H); ESI MS m/z 411 [M+H]+

Sources & evidence

ORD record
ord-3a240d0d7b604afda3eb25ffa61b043c
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

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