Pyridine → N-(2-amino-4-methoxy-benzothiazol-7-yl)-N-methyl-acetamide

HRID 51875Notes

Reaction equation

HRID 51875 reaction equation
COC1C2[N:9]=[C:10]([NH2:12])[S:11][C:7]=2[C:6]([NH:13][CH3:14])=[CH:5][CH:4]=1.N1C=CC=C[CH:16]=1.[C:21](Cl)(=[O:23])[CH3:22].[O:25]1CC[CH2:27][CH2:26]1>ClCCl>[NH2:12][C:10]1[S:11][C:7]2[C:6]([N:13]([CH3:14])[C:26](=[O:25])[CH3:27])=[CH:5][CH:4]=[C:21]([O:23][CH3:16])[C:22]=2[N:9]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 227369784-methoxy-N7-methyl-benzothiazole-2,7-diamine

Product 1

HCID 22736969N-(2-amino-4-methoxy-benzothiazol-7-yl)-N-methyl-acetamideYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 120 mg (0.57 mmol) 4-methoxy-N7-methyl-benzothiazole-2,7-diamine in 1 ml dichloromethane and 1 ml tetrahydrofuran at 0° C. was added 0.09 ml (1.15 mmol) pyridine. A solution of 0.04 ml (0.57 mmol) acetyl chloride in 1 ml dichloromethane was then added dropwise and stirring continued for 3 h at 0° C. The mixture was then concentrated in vacuo. Flash chromatography (30/1 dichloromethane/methanol) afforded 60 mg (42%) N-(2-amino-4-methoxy-benzothiazol-7-yl)-N-methyl-acetamide as a light brown crystalline solid, ES-MS m/e (%): 252 (M+H+, 100).

Workup

  1. concentrationThe mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-43d2250b24964c68be75b2cb7cce2fb5
Source dataset
uspto-grants-2004_03
Patent number
US06713499B2

Reaction notes

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