4-Methylmorpholine → HCID 21968056, compound

HRID 1004730Notes

Reaction equation

HRID 1004730 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:12][CH2:11][C:10]3[CH:13]=[C:14]([Cl:18])[CH:15]=[C:16]([Br:17])[C:9]=3[C@@H:8]([CH:19]3[CH2:24][CH2:23][N:22]([C:25](=[O:40])[CH2:26][C:27]4([C:37](O)=O)[CH:32]=[CH:31][N:30]([S:33]([CH3:36])(=[O:35])=[O:34])[CH:29]=[CH:28]4)[CH2:21][CH2:20]3)[C:5]2=[N:6][CH:7]=1.O.O[N:43]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[Cl-].[NH4+].CN1CCOCC1>CN(C)C=O.ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:12][CH2:11][C:10]3[CH:13]=[C:14]([Cl:18])[CH:15]=[C:16]([Br:17])[C:9]=3[C@@H:8]([CH:19]3[CH2:24][CH2:23][N:22]([C:25](=[O:40])[CH2:26][C:27]4([C:37]#[N:43])[CH:32]=[CH:31][N:30]([S:33]([CH3:36])(=[O:34])=[O:35])[CH:29]=[CH:28]4)[CH2:21][CH2:20]3)[C:5]2=[N:6][CH:7]=1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 25517Ammonium ChlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 21968055HCID 21968055, compound

Product 1

HCID 21968056HCID 21968056, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Dissolve the title compound from Example 2 (1 mmol) in anhydrous N,N-dimethylformamide (DMF, 10 mL) and add 1-hydroxybenzotriazole hydrate (1 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1 mmol), ammonium chloride (1 mmol) and N-methylmorpholine (1 mmol). Stir the resulting mixture at room temperature under nitrogen overnight. Concentrate in vacuo to provide a residue and dilute with dichloromethane, wash with 1M hydrochloric acid and brine, then dry over anhydrous magnesium sulfate. Filter and concentrate in vacuo to afford (+)-4-(3,10-dibromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11(R)-yl)-1-[[4-cyano-1-(methylsulfonyl)-4-pyridinyl]acetyl]piperidine.

Workup

  1. concentrationConcentrate in vacuo
  2. customto provide a residue
  3. washwash with 1M hydrochloric acid and brine
  4. dry with materialdry over anhydrous magnesium sulfate
  5. filtrationFilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-4786edea52e84e62ab5ed1bed3f61165
Source dataset
uspto-grants-2000_04
Patent number
US06051582

Reaction notes

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