4-(Chloromethyl)benzoyl chloride → HCID 22719566, compound

HRID 1582111Notes

Reaction equation

HRID 1582111 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH2:12])[S:11][C:7]=2[C:6]([CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:5][CH:4]=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>C1COCC1.ClCCl>[Cl:28][CH2:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([NH:12][C:10]2[S:11][C:7]3[C:6]([CH:13]4[CH2:18][CH2:17][O:16][CH2:15][CH2:14]4)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=3[N:9]=2)=[O:35])=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 701364-(Chloromethyl)benzoyl chlorideHCID 81531DiisopropylethylamineHCID 220157354-Methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl-amine

Product 1

HCID 22719566HCID 22719566, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 250 mg (0.95 mmol) 4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-ylamine and 0.95 ml (5.53 mmol) N-ethyldiisopropylamine in 10 ml THF at room temperature was added dropwise a solution of 216 mg (1.14 mmol) 4-(chloromethyl)benzoyl chloride in 3 ml dichloromethane and stirring continued at room temperature for 60 h. The reaction mixture was then concentrated in vacuo. Flash chromatography (1/1 ethyl acetate/hexane) followed by trituration in ether afforded 280 mg (71%) 4-chloromethyl-N-[4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl]-benzamide as a white crystalline solid. ES-MS m/e (%): 441 (M{37Cl}+Na+, 7), 439 (M{35Cl}+Na+, 21). 419 (M{37Cl}+H+, 41), 417 (M{35Cl}+H+, 100).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-89655537c0ef4b4bb327f579c197dd65
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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