Pyridine → 5-Methyl-thiophene-2-carboxylic acid (7-bromo-4-methoxybenzothiazol-2-yl)-amide

HRID 1062990Notes

Reaction equation

HRID 1062990 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:10]([Br:11])=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[C:5]=2[N:6]=1.N1C=CC=CC=1.[CH3:20][C:21]1[S:25][C:24]([C:26](Cl)=[O:27])=[CH:23][CH:22]=1>ClCCl>[Br:11][C:10]1[C:4]2[S:3][C:2]([NH:1][C:26]([C:24]3[S:25][C:21]([CH3:20])=[CH:22][CH:23]=3)=[O:27])=[N:6][C:5]=2[C:7]([O:12][CH3:13])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 27600835-Methylthiophene-2-carbonyl chlorideHCID 222832007-Bromo-4-methoxy-1,3-benzothiazol-2-amine

Product 1

HCID 865849105-Methyl-thiophene-2-carboxylic acid (7-bromo-4-methoxybenzothiazol-2-yl)-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Amino-7-bromo-4-methoxybenzothiazol (2.33 g, 9 mmol) is dissolved in dichloromethane (100 ml) and at 0° C. treated with pyridine (2.2 ml, 27 mmol) and 5-methyl-thiophene-2-carbonyl chloride (2.2 g, 13.5 mmol). The reaction mixture is allowed to warm to room temperature and after stirring for additional 18 h quenched with water (100 ml). After separation of the phases, the aqueous phases are extracted twice with ethyl acetate. The combined organic layers are then washed with brine, dried and avaporated to dryness. Flash chromatography on silica (eluent ethyl acetate/cyclohexane 1:1 to 4:1) and final recrystallization from ethyl acetate affords the product as off-white solid. (34 mg, 69%). MS: m/e=384 (M+).

Workup

  1. customquenched with water (100 ml)
  2. customAfter separation of the phases
  3. extractionthe aqueous phases are extracted twice with ethyl acetate
  4. washThe combined organic layers are then washed with brine
  5. customdried
  6. customFlash chromatography on silica (eluent ethyl acetate/cyclohexane 1:1 to 4:1) and final recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-b364f833212d4f4dbee98309439f950b
Source dataset
uspto-grants-2005_11
Patent number
US06963000B2

Reaction notes

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