Pyridine → HCID 10195477, compound

HRID 1167774Notes

Reaction equation

HRID 1167774 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.Cl[C:37]([O:39][CH3:40])=[O:38].C(=O)([O-])O.[Na+]>O1CCCC1.ClCCl.CO>[CH3:40][O:39][C:37](=[O:38])[N:21]([CH2:20][C:16]1[CH:15]=[C:14]([C:13](=[O:23])[NH:12][C:10]2[S:11][C:7]3[C:6]([N:24]4[CH2:25][CH2:26][O:27][CH2:28][CH2:29]4)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=3[N:9]=2)[CH:19]=[CH:18][N:17]=1)[CH3:22]

Participants

7

Reactant 4

HCID 1049Pyridine2×HCID 6586Methyl chloroformate2×HCID 516892Sodium BicarbonateHCID 10223485HCID 10223485, compound

Product 1

HCID 10195477HCID 10195477, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-2-methylaminomethyl-isonicotinamide (180 mg, 0.44 mmol) in tetrahydrofurane(15 ml) is subsequently treated with pyridine(52 μl, 0.65 mmol) and methyl chloroformate (43 μl, 0.57 mmol)and stirred at ambient temperature for 15 h. Additional pyridine (25 μl, 0.31 mmol) and methylchloroformate (20 μl, 0.26 mmol) are added and the mixture stirred for another hour. Saturated sodium hydrogen carbonate (15 ml) is added and the mixture extracted four times with ethyl acetate. The combined organic ohases are dried with magnesium sulfate and evaporated to dryness. Flash chromatography (SiO2, eluent: dichloromethane/methanol 19:1) afforded the title compound as yellow crystals (115 mg, 56% yield). MS: m/e=472 (M+H+).

Workup

  1. stirringthe mixture stirred for another hour
  2. extractionthe mixture extracted four times with ethyl acetate
  3. dry with materialThe combined organic ohases are dried with magnesium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-d8d131142fc343e3a676262f14c15a07
Source dataset
uspto-grants-2003_09
Patent number
US06620811B2

Reaction notes

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