(2-Methoxyethyl)(methyl)amine → HCID 86597266, compound

HRID 917444Notes

Reaction equation

HRID 917444 reaction equation
Cl[CH2:2][C:3]1[CH:28]=[CH:27][C:6]([C:7]([NH:9][C:10]2[S:11][C:12]3[C:13]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[N:14][CH:15]=[C:16]([O:19][CH3:20])[C:17]=3[N:18]=2)=[O:8])=[CH:5][CH:4]=1.[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:28]=[CH:27][C:6]([C:7]([NH:9][C:10]2[S:11][C:12]3[C:13]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[N:14][CH:15]=[C:16]([O:19][CH3:20])[C:17]=3[N:18]=2)=[O:8])=[CH:5][CH:4]=1)[CH3:34]

Participants

3

Reactant 2

HCID 300977(2-Methoxyethyl)(methyl)amineHCID 86597265HCID 86597265, compound

Product 1

HCID 86597266HCID 86597266, compoundYield 62.1%

Procedure

A solution of 60 mg (0.14 mmol) 4-chloromethyl-N-(7-methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-yl)-benzamide in 0.30 ml (2.70 mmol) N-(2-methoxyethyl)methylamine was ultrasonicated at room temperature for 40 min. The reaction mixture was then concentrated in vacuo. Flash chromatography (methanol/dichloromethane) followed by trituration in ether afforded 41 mg (61%) 4-{[(2-methoxy-ethyl)-methyl-amino]-methyl}-N-(7-methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-yl)-benzamide as a white crystalline solid. ES-MS m/e (%): 472 (M+H+, 100).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-4d74bb4d8295405ca267122539d47f9a
Source dataset
uspto-grants-2007_09
Patent number
US07273865B2

Reaction notes

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