Water → HCID 18917540, compound

HRID 1290960Notes

Reaction equation

HRID 1290960 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][C:24]([C:26]4[C:27](Cl)=[N:28][CH:29]=[CH:30][CH:31]=4)=[O:25])=[CH:19][CH:18]=3)=[O:16])[CH2:6][C:5]=12.C([O-])([O-])=O.[K+].[K+].[CH3:39][NH2:40].O>CS(C)=O>[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][C:24]([C:26]4[C:27]([NH:40][CH3:39])=[N:28][CH:29]=[CH:30][CH:31]=4)=[O:25])=[CH:19][CH:18]=3)=[O:16])[CH2:6][C:5]=12

Participants

6

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 11430Potassium CarbonateHCID 18917489HCID 18917489, compound

Product 1

HCID 18917540HCID 18917540, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 1 g of N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-2-chloropyridine-3-carboxamide, 1 g of K2CO3 and 10 ml of a 40% solution of monomethylamine is heated in 25 ml of dimethylsulfoxide for 8 hours at 100° C. The reaction mixture is poured over water and the pale yellow solid separated. The reaction mixture is filtered and the collected solid washed well with water. After drying the solid is purified by column chromatography on silica gel by elution with 9:1 ethyl acetate:methanol to give 850 mg of the desired product as a pale yellow solid: M+ =437.

Workup

  1. customthe pale yellow solid separated
  2. filtrationThe reaction mixture is filtered
  3. washthe collected solid washed well with water
  4. customAfter drying the solid
  5. customis purified by column chromatography on silica gel by elution with 9:1 ethyl acetate

Sources & evidence

ORD record
ord-789fe77449e5417da5fe50145c57028b
Source dataset
uspto-grants-1998_05
Patent number
US05753648

Reaction notes

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