4-Methylmorpholine → HCID 20740233, compound

HRID 1883136Notes

Reaction equation

HRID 1883136 reaction equation
[C:1]([C@@H:3]([NH:9][C:10]([C@@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]1[NH:18][C:19]([C:21]1[N:22]([CH3:30])[C:23]2[C:28]([CH:29]=1)=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])=[O:11])[CH2:4][CH2:5][C:6]([OH:8])=O)#[N:2].[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C>[C:1]([C@@H:3]([NH:9][C:10]([C@@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]1[NH:18][C:19]([C:21]1[N:22]([CH3:30])[C:23]2[C:28]([CH:29]=1)=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])=[O:11])[CH2:4][CH2:5][C:6]([N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1)=[O:8])#[N:2]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 20740244HCID 20740244, compound

Product 1

HCID 20740233HCID 20740233, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The (S)-4-cyano-4-({(1R,2S)-2-[(1-methyl-1H-indole-2-carbonyl)-amino]-cyclohexanecarbonyl}-amino)-butyric acid (140 mg, 0.341 mmol), morpholine (50 μL, 0.57 mmol), EDCI hydrochloride (102 mg, 0.532 mmol), HOBT (50 mg, 0.37 mmol) and N-methyl morpholine (0.10 mL, 0.91 mmol) were dissolved in 5.0 mL of DMF and stirred at room temp for 4 hours. The reaction mixture was partitioned between 50 mL of water and 50 mL of ethyl acetate. The organic layer was washed with water (2×50 mL), dried with sodium sulfate, filtered and concentrated to give 98 mg (60%) of 1-Methyl-1H-indole-2-carboxylic acid [(1S,2R)-2-((S)-1-cyano-4-morpholin-4-yl-4-oxo-butylcarbamoyl)-cyclohexyl]-amide as a white amorphous solid. MS: 480 (M+H+).

Workup

  1. customThe reaction mixture was partitioned between 50 mL of water and 50 mL of ethyl acetate
  2. washThe organic layer was washed with water (2×50 mL)
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-82b8a17e366c49b2bade32ff48db4fc5
Source dataset
uspto-grants-2004_07
Patent number
US06759428B2

Reaction notes

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