Diethylamine → (+)-2-Diethylaminomethyl-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide

HRID 985810Notes

Reaction equation

HRID 985810 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][N:28]=1)[C:6]([NH:8][C:9]1[S:10][C:11]2[C:17]([CH:18]3[CH2:23][O:22][CH2:21][CH2:20][O:19]3)=[CH:16][CH:15]=[C:14]([O:24][CH3:25])[C:12]=2[N:13]=1)=[O:7].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:35]([NH:37][CH2:38][CH3:39])[CH3:36]>C(Cl)(Cl)Cl>[CH2:35]([N:37]([CH2:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][N:28]=1)[C:6]([NH:8][C:9]1[S:10][C:11]2[C:17]([CH:18]3[CH2:23][O:22][CH2:21][CH2:20][O:19]3)=[CH:16][CH:15]=[C:14]([O:24][CH3:25])[C:12]=2[N:13]=1)=[O:7])[CH2:38][CH3:39])[CH3:36]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 10796Cesium carbonateHCID 22507718(+)-2-chloromethyl-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide

Product 1

HCID 22507749(+)-2-Diethylaminomethyl-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

From (+)-2-chloromethyl-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide with cesium carbonate and diethylamine. [α]D20=+48.9° (c=1.02, CHCl3), ES-MS m/e (%): 457 (M+H+, 100).

Sources & evidence

ORD record
ord-ddcf89b90e304643a34bf1af3935db7e
Source dataset
uspto-grants-2005_03
Patent number
US06872833B2

Reaction notes

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