Pyridine → HCID 22993391, compound

HRID 1167805Notes

Reaction equation

HRID 1167805 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH:12][C:13](=[O:23])[C:14]3[CH:19]=[CH:18][N:17]=[C:16]([CH2:20][NH:21][CH3:22])[CH:15]=3)[S:11][C:7]=2[C:6]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[CH:5][CH:4]=1.N1C=CC=CC=1.[C:36](Cl)(=[O:38])[CH3:37].C(=O)([O-])O.[Na+]>ClCCl>[C:36]([N:21]([CH2:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][N:17]=1)[C:13]([NH:12][C:10]1[S:11][C:7]2[C:6]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=2[N:9]=1)=[O:23])[CH3:22])(=[O:38])[CH3:37]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 10223485HCID 10223485, compound

Product 1

HCID 22993391HCID 22993391, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-2-methylaminomethyl-isonicotinamide (207 mg, 0.5 mmol) is dissolved in dichloromethane (10 ml) and treated with pyridine (0.07 ml, 0.85 mmol) and acetyl chloride (0.05 ml, 0.7 mmol) and stirred for 16 h at ambient temperature. Saturated aqueous sodium hydrogen carbonate (10 ml) is added, the layers are separated and the aqueous phase extracted twice with each 10 ml dichloromethane. The combined organic phases are dried with magnesium sulfate and evaporated. Recrystallization from ethyl acetate afforded the title compound as light-yellow solid (80% yield), mp 228-230° C. MS: m/e=456 (M+H+).

Workup

  1. customthe layers are separated
  2. extractionthe aqueous phase extracted twice with each 10 ml dichloromethane
  3. dry with materialThe combined organic phases are dried with magnesium sulfate
  4. customevaporated
  5. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-b8249780965442bbbd24f58a234459e6
Source dataset
uspto-grants-2003_09
Patent number
US06620811B2

Reaction notes

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