Dimethylamine, hydrochloride → HCID 131730107, compound

HRID 2192956Notes

Reaction equation

HRID 2192956 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C@@H:16]([CH2:29][C@H:30]3[CH2:34][CH2:33][C:32](=[O:35])[CH2:31]3)[C:17]([NH:19][C:20]3[N:21]=[CH:22][C:23]([C:26](O)=O)=[N:24][CH:25]=3)=[O:18])[CH:7]=[CH:8][C:9]=2[S:10]([CH:13]2[CH2:15][CH2:14]2)(=[O:12])=[O:11])[CH2:3][CH2:2]1.[OH:36]N1C2C=CC=CC=2N=N1.Cl.[CH3:47][N:48]([CH3:57])[CH2:49]CCN=C=NCC.Cl.CNC>CN(C=O)C.O.C(N(CC)CC)C>[CH:1]1([C:4]2[CH:5]=[C:6]([C@@H:16]([CH2:29][C@H:30]3[CH2:34][CH2:33][C:32](=[O:35])[CH2:31]3)[C:17]([NH:19][C:20]3[N:21]=[CH:22][C:23]([CH2:26][C:49]([N:48]([CH3:57])[CH3:47])=[O:36])=[N:24][CH:25]=3)=[O:18])[CH:7]=[CH:8][C:9]=2[S:10]([CH:13]2[CH2:14][CH2:15]2)(=[O:11])=[O:12])[CH2:2][CH2:3]1

Participants

8

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 595708805-[[(2R)-2-[3-Cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-1-oxo-3-[(1R)-3-oxocyclopentyl]propyl]amino]-2-pyrazinecarboxylic acid

Product 1

HCID 131730107HCID 131730107, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 5-({(2R)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-[(1R)-3-oxocyclopentyl]propanoyl}amino)pyrazine-2-carboxylic acid (102 mg), 1-hydroxybenzotriazole (44 mg), and N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide monohydrochloride (59 mg) in DMF (5 mL) were added dimethylamine monohydrochloride (22 mg) and triethylamine (0.09 mL) at room temperature. The reaction mixture was stirred at room temperature overnight, and water was then added thereto for liquid separation. The organic layer was sequentially washed with 1 M hydrochloric acid, saturated aqueous sodium bicarbonate, and saturated brine, and dried over anhydrous magnesium sulfate. The crude product obtained by concentration was purified by silica gel column chromatography (wetting with hexane:ethyl acetate=1:1, chloroform:methanol=1:0-10:1) to obtain 5-({(2R)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-[(1R)-3-oxocyclopentyl]propanoyl}amino)-N,N-dimethylpyrazine-2-carboxyamide (64 mg) as a pale yellow amorphous substance.

Workup

  1. customfor liquid separation
  2. washThe organic layer was sequentially washed with 1 M hydrochloric acid, saturated aqueous sodium bicarbonate, and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe crude product obtained by concentration
  5. customwas purified by silica gel column chromatography (wetting with hexane:ethyl acetate=1:1, chloroform:methanol=1:0-10:1)

Sources & evidence

ORD record
ord-e51a0a18ece3420490d32531f60e49e8
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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