Sarcosine → HCID 178427389, compound

HRID 74457Notes

Reaction equation

HRID 74457 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:16]=[CH:15][C:10]3[NH:11][C:12]([CH3:14])=[N:13][C:9]=3[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:17]([C:19]1[N:20]([S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[C:23](I)[CH:22]=2)=[O:18].[CH3:39][S:40]([NH2:43])(=[O:42])=[O:41].N(CC(O)=O)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl-].[NH4+]>CN1CCCC1=O.[Cu]I>[NH2:1][C:2]1[N:6]([C:7]2[CH:16]=[CH:15][C:10]3[NH:11][C:12]([CH3:14])=[N:13][C:9]=3[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:17]([C:19]1[N:20]([S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[C:23]([NH:43][S:40]([CH3:39])(=[O:42])=[O:41])[CH:22]=2)=[O:18]

Participants

8

Reactant 5

HCID 1088SarcosineHCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 72879MethanesulfonamideHCID 178427388HCID 178427388, compound

Product 1

HCID 178427389HCID 178427389, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

[5-Amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-[6-iodo-1-(toluene-4-sulfonyl)-1H-indol-2-yl]-methanone (80.3 mg, 0.126 mmol), copper (I) iodide (37.5 mg, 0.197 mmol), methanesulfonamide (37.5 mg, 0.394 mmol), sarcosine (36.2 mg, 0.406 mmol), and tripotassium phosphate (86.0 mg, 9.405 mmol) were dissolved in anhydrous 1-methyl-2-pyrrolidinone (0.36 ml), and heated at 140° C. with stirring under an argon atmosphere for 30 minutes. The reaction mixture was added dropwise to an aqueous solution (20 ml) of 20% ammonium chloride, and extracted with ethyl acetate, the organic layer was washed with an aqueous solution of 20% sodium chloride and dried over anhydrous sodium sulfate. The desiccant was removed by filtration. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by amino gel column chromatography (dichloromethane/methanol=15/1) to give N-[2-[5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazole-4-carbonyl]-1-(toluene-4-sulfonyl)-1H-indol-6-yl]methanesulfonamide as a yellow amorphous material (17.9 mg with a yield of 24%).

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic layer was washed with an aqueous solution of 20% sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe desiccant was removed by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe resulting residue was purified by amino gel column chromatography (dichloromethane/methanol=15/1)

Sources & evidence

ORD record
ord-96c1e5db954e4ec1a7ac7330c7085730
Source dataset
uspto-grants-2014_09
Patent number
US08829199B2

Reaction notes

Loading…