(2-Methoxyethyl)(methyl)amine → 2-{[(2-Methoxy-ethyl)-methyl-amino]-methyl}-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-isonicotinamide

HRID 1167773Notes

Reaction equation

HRID 1167773 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]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:16][CH:15]=[C:14]([O:24][CH3:25])[C:12]=2[N:13]=1)=[O:7].[CH3:29][O:30][CH2:31][CH2:32][NH:33][CH3:34]>>[CH3:29][O:30][CH2:31][CH2:32][N:33]([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]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:16][CH:15]=[C:14]([O:24][CH3:25])[C:12]=2[N:13]=1)=[O:7])[CH3:34]

Participants

3

Reactant 2

HCID 300977(2-Methoxyethyl)(methyl)amineHCID 229933982-Chloromethyl-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-isonicotinamide

Product 1

HCID 229934162-{[(2-Methoxy-ethyl)-methyl-amino]-methyl}-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-isonicotinamide

Conditions

Temperature
60 °C

Procedure

2-Chloromethyl-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-isonicotinamide (240 mg, 0.55 mmol) is dissolved in N-(2-methoxyethyl)-methylamine (1.0 g, 12 mmol) and the mixture heated to 60° C. for 1 h. The volatile components are removed in vacuo and the residue chromatographed over SiO2 eluting with dichloromethane/methanol 19/1. The title compound was obtained as yellow crystals (170 mg, 71% yield). MS: m/e=472(M+H+). Following the general method of example 46 the compounds of examples 47-62 were prepared.

Workup

  1. customThe volatile components are removed in vacuo
  2. customthe residue chromatographed over SiO2 eluting with dichloromethane/methanol 19/1

Sources & evidence

ORD record
ord-ef75036149ec4effaec35914e979c121
Source dataset
uspto-grants-2003_09
Patent number
US06620811B2

Reaction notes

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