4-Methylmorpholine → HCID 20740235, compound

HRID 1883156Notes

Reaction equation

HRID 1883156 reaction equation
[NH2:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][C@H:7]([NH:10][C:11]([C@@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C@@H:14]2[NH:19][C:20]([C:22]2[N:23]([CH3:31])[C:24]3[C:29]([CH:30]=2)=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])=[O:12])[C:8]#[N:9])=[CH:4][CH:3]=1.[CH3:34][S:35](Cl)(=[O:37])=[O:36].CN1CCOCC1>CN(C=O)C.CN(C)C1C=CN=CC=1>[C:8]([C@@H:7]([NH:10][C:11]([C@@H:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C@@H:14]1[NH:19][C:20]([C:22]1[N:23]([CH3:31])[C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])=[O:12])[CH2:6][C:5]1[CH:4]=[CH:3][C:2]([NH:1][S:35]([CH3:34])(=[O:37])=[O:36])=[CH:33][CH:32]=1)#[N:9]

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 31297Methanesulfonyl chlorideHCID 20740234HCID 20740234, compound

Product 1

HCID 20740235HCID 20740235, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To 62 mg (0.14 mmol) of 1-methyl-1H-indole-2-carboxylic acid ((1S,2R)-2-{[(S)-(4-amino-benzyl)cyano-methyl]-carbamoyl}cyclohexyl)-amide dissolved in 1 mL DMF was added 16 mg (0.14 mmol) of methanesulfonyl chloride, 2 mg (0.014 mmol) of 4-dimethylaminopyridine, and 0.031 mL (0.28 mmol) of N-methylmorpholine. The reaction mixture was stirred at room temperature overnight, partitioned between ethyl acetate and water, dried over magnesium sulfate, and concentrated. Reverse phase column chromatography was employed to separate the pure title compound from the unreacted starting material, and provided 10 mg of 1-methyl-1H-indole-2-carboxylic acid ((1S,2R)-2-{[(S)-cyano-(4-methanesulfonylamino-benzyl)-methyl]-carbamoyl}-cyclohexyl)-amide. HPLC: 100% pure, yield: 14%, MS: 522 (M+H+).

Workup

  1. custompartitioned between ethyl acetate and water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customto separate the pure title compound from the

Sources & evidence

ORD record
ord-63745b39c9924ba6b4246dcda3342f7e
Source dataset
uspto-grants-2004_07
Patent number
US06759428B2

Reaction notes

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