Methylamine → HCID 69107981, compound

HRID 1838261Notes

Reaction equation

HRID 1838261 reaction equation
C1C=CC2N(O)N=[N:7][C:5]=2C=1.CCN=C=NCCCN(C)C.[C:22]([C:24]1[CH:29]=[CH:28][C:27]([N:30]2[C@@H:35]([CH3:36])[CH2:34][N:33]([C:37]([NH:39][C:40]3[CH:45]=[CH:44][N:43]=[C:42]([C:46]([OH:48])=O)[CH:41]=3)=[O:38])[C@H:32]([CH3:49])[CH2:31]2)=[CH:26][C:25]=1[C:50]([F:53])([F:52])[F:51])#[N:23].CN>CN(C=O)C.O>[C:22]([C:24]1[CH:29]=[CH:28][C:27]([N:30]2[C@@H:35]([CH3:36])[CH2:34][N:33]([C:37]([NH:39][C:40]3[CH:45]=[CH:44][N:43]=[C:42]([C:46](=[O:48])[NH:7][CH3:5])[CH:41]=3)=[O:38])[C@H:32]([CH3:49])[CH2:31]2)=[CH:26][C:25]=1[C:50]([F:52])([F:51])[F:53])#[N:23]

Participants

7

Reactant 4

HCID 6329MethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 69108009HCID 69108009, compound

Product 1

HCID 69107981HCID 69107981, compoundYield 59.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Under ice-cooling, 332 mg of HOBT and 519 mg of WSC were added in that order to a suspension of 1.10 g of (2R,5S)-4-{[4-(4-cyano-3-trifluoromethylphenyl)-2,5-dimethylpiperazine-1-carbonyl]amino}pyridine-2-carboxylic acid synthesized in Example 12-1 in 30 ml of DMF, and then the mixture was warmed up to room temperature and stirred for 1.5 hours. This was again ice-cooled, 10 ml of 40% aqueous methylamine was added thereto in one portion and then the mixture was stirred overnight. This was mixed with purified water and extracted with ethyl acetate, and the thus obtained organic layer was washed twice with saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to a silica gel column chromatography to obtain 674 mg of the title compound from methanol-ethyl acetate (1:9, v/v) eluate.

Workup

  1. temperatureUnder ice-cooling
  2. temperaturecooled
  3. stirringin one portion and then the mixture was stirred overnight
  4. extractionextracted with ethyl acetate
  5. washthe thus obtained organic layer was washed twice with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c2f711dc3db0472f98cb6735e4258026
Source dataset
uspto-grants-2004_01
Patent number
US06673799B1

Reaction notes

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