4-(Chloromethyl)benzoyl chloride → HCID 86597265, compound

HRID 917443Notes

Reaction equation

HRID 917443 reaction equation
[CH3:1][O:2][C:3]1[C:4]2[N:17]=[C:16]([NH2:18])[S:15][C:5]=2[C:6]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[N:7][CH:8]=1.C(N(C(C)C)C(C)C)C.[Cl:28][CH2:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1>ClCCCl.C1COCC1>[Cl:28][CH2:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([NH:18][C:16]2[S:15][C:5]3[C:6]([N:9]4[CH2:10][CH2:11][O:12][CH2:13][CH2:14]4)=[N:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=3[N:17]=2)=[O:35])=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 701364-(Chloromethyl)benzoyl chlorideHCID 81531DiisopropylethylamineHCID 860385537-Methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-ylamine

Product 1

HCID 86597265HCID 86597265, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 150 mg (0.56 mmol) 7-methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-ylamine in 3 ml 1,2-dichloroethane and 3 ml THF at room temperature were added 0.29 ml (1.69 mmol) N-ethyldiisopropylamine and 117 mg (0.62 mmol) 4-(chloromethyl)benzoyl chloride and stirring continued at 80° C. for 2 h. The reaction mixture was then cooled to room temperature and concentrated in vacuo. Flash chromatography (ethyl acetate/heptane) afforded 157 mg (67%) 4-chloromethyl-N-(7-methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-yl)-benzamide as a yellow solid. ES-MS m/e (%):421 (M{37Cl}+H+, 35), 419 (M{35Cl}+H+, 100).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-51dfc93b66904c7783b3cb7a7e56736a
Source dataset
uspto-grants-2007_09
Patent number
US07273865B2

Reaction notes

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