4,6-Dichloro-1,5-naphthyridin-3-yl(cyclopropyl) methanone → HCID 178483667, compound

HRID 526176Notes

Reaction equation

HRID 526176 reaction equation
[CH:1]1([C:4]([C:6]2[CH:7]=[N:8][C:9]3[C:14]([C:15]=2Cl)=[N:13][C:12]([Cl:17])=[CH:11][CH:10]=3)=[O:5])[CH2:3][CH2:2]1.C(O)(=O)C.C(O)(=O)C.[CH3:26][N:27]([CH2:29][C@H:30]1[CH2:35][CH2:34][C@H:33]([NH2:36])[CH2:32][CH2:31]1)[CH3:28]>>[Cl:17][C:12]1[N:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:4]([CH:1]1[CH2:3][CH2:2]1)=[O:5])=[C:15]2[NH:36][C@H:33]1[CH2:34][CH2:35][C@H:30]([CH2:29][N:27]([CH3:28])[CH3:26])[CH2:31][CH2:32]1

Participants

3

Reactant 2

HCID 897056244,6-Dichloro-1,5-naphthyridin-3-yl(cyclopropyl) methanoneHCID 178476567HCID 178476567, compound

Product 1

HCID 178483667HCID 178483667, compoundYield 39%

Procedure

Following general procedure I, cyclopropyl(4,6-dichloro-1,5-naphthyridin-3-yl)-methanone (267 mg, 1.0 mmol) was reacted with trans-4-[(dimethylamino)methyl]cyclohexanamine diacetic acid salt (270 mg, 1.0 mmol) to afford the desired product (150 mg, 39%) as an off-white solid: 1H NMR (500 MHz, CDCl3) δ 10.85 (br s, 1H), 9.19 (s, 1H), 8.08 (d, J=8.7 Hz, 1H), 7.51 (d, J=8.7 Hz, 1H), 4.97 (br s, 1H), 2.72-2.62 (m, 1H), 2.31-2.24 (m, 2H), 2.22 (s, 6H), 2.13 (d, J=7.2 Hz, 2H), 1.96-1.89 (m, 2H), 1.55-1.46 (m, 1H), 1.36 (qd, J=12.4, 3.3 Hz, 2H), 1.28-1.22 (m, 2H), 1.21-1.09 (m, 2H), 1.08-1.02 (m, 2H); ESI MS m/z 387 [M+H].+

Sources & evidence

ORD record
ord-9ad5d23076304b9792a399acce583665
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

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