4-Methylmorpholine → HCID 18450643, compound

HRID 2390617Notes

Reaction equation

HRID 2390617 reaction equation
[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][S:10][C:6]=2[C:5](/[CH:17]=[CH:18]/[C:19]([OH:21])=O)=[CH:4][N:3]=1.Cl.CN.C1C=CC2N(O)N=[N:31][C:29]=2C=1.CN1CCOCC1.CCN=C=NCCCN(C)C>CN(C=O)C.O>[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][S:10][C:6]=2[C:5](/[CH:17]=[CH:18]/[C:19]([NH:31][CH3:29])=[O:21])=[CH:4][N:3]=1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 6364545Methylamine hydrochlorideHCID 18450642HCID 18450642, compound

Product 1

HCID 18450643HCID 18450643, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 13 (0.1 g, 0.34 mmol), methylamine hydrochloride (0.115 g, 1.69 mmol), HOBT (0.137 g, 1.01 mmol), N-methylmorpholine (0.25 mL, 2.36 mmol), and EDCI (0.199 g, 1.01 mmol) in DMF (5 mL) was stirred at room temperature for 2 hours, diluted with water (20 mL), and extracted with ethyl acetate (2×20 mL). The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated to provide 89 mg of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 2.73 (d, J=4.8 Hz, 3H), 5.75-5.85 (br s, 2H), 6.58 (d, J=15.9 Hz, 1H), 7.53 (m, 5H), 7.58 (d, J=15.9 Hz, 1H), 7.67 (s, 1H), 8.14 (m, 2H); MS (ESI(+)) m/e 310 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (2×20 mL)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-928d285c430a4fc6ad7d97d7bc276a47
Source dataset
uspto-grants-2012_09
Patent number
US08273736B2

Reaction notes

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