1-(4,6-Dichloro-1,5-naphthyridin-3-yl)ethan-1-one → HCID 178467150, compound

HRID 2178929Notes

Reaction equation

HRID 2178929 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].[C:16]([O:20][C:21](=[O:30])[NH:22][C@H:23]1[CH2:28][CH2:27][C@H:26]([NH2:29])[CH2:25][CH2:24]1)([CH3:19])([CH3:18])[CH3:17]>>[C:13]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:29][C@H:26]1[CH2:27][CH2:28][C@H:23]([NH:22][C:21](=[O:30])[O:20][C:16]([CH3:18])([CH3:17])[CH3:19])[CH2:24][CH2:25]1)=[N:10][C:9]([Cl:12])=[CH:8][CH:7]=2)(=[O:15])[CH3:14]

Participants

3

Reactant 2

HCID 897049771-(4,6-Dichloro-1,5-naphthyridin-3-yl)ethan-1-oneHCID 178419079HCID 178419079, compound

Product 1

HCID 178467150HCID 178467150, compoundYield 71.6%

Procedure

Following general procedure I, 1-(4,6-dichloro-1,5-naphthyridin-3-yl)ethanone (480 mg, 2.0 mmol) was reacted with tert-butyl(trans-4-aminocyclohexyl)carbamate (430 mg, 2.0 mmol) to afford the desired product (600 mg, 71%) as a light orange solid: 1H NMR (500 MHz, CDCl3) δ 10.91 (br s, 1H), 8.96 (s, 1H), 8.10 (d, J=8.8 Hz, 1H), 7.54 (d, J=8.8 Hz, 1H), 5.10-4.99 (m, 1H), 4.48 (br s, 1H), 3.55 (br s, 1H), 2.69 (s, 3H), 2.34-2.25 (m, 2H), 2.19-2.10 (m, 2H), 1.56-1.45 (m, 2H), 1.47 (s, 9H), 1.44-1.33 (m, 2H);

Sources & evidence

ORD record
ord-4119f7dc857a470ab8f7679e440977bc
Source dataset
uspto-grants-2015_06
Patent number
US09067937B2

Reaction notes

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