4-Methylmorpholine → HCID 9889061, compound

HRID 1940663Notes

Reaction equation

HRID 1940663 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:15]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:22]=1.CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.[N:40]1[CH:45]=[CH:44][C:43]([CH2:46][C:47](O)=[O:48])=[CH:42][CH:41]=1>CN(C=O)C.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:15]([N:16]3[CH2:17][CH2:18][N:19]([C:47](=[O:48])[CH2:46][C:43]4[CH:44]=[CH:45][N:40]=[CH:41][CH:42]=4)[CH2:20][CH2:21]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:22]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 342284-Pyridineacetic acidHCID 757711-HydroxybenzotriazoleHCID 5255691HCID 5255691, compound

Product 1

HCID 9889061HCID 9889061, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 8.5 g (27.2 m mole) of 8-chloro-11-(1-piperazinyl)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine (Preparative Example 7) in 256 mL of anhydrous DMF at room temperature and under an argon atmosphere was added 2.98 g (27.2 m mole of 4-methyl-morpholine, 7.81 g (27.2 m mole) of DEC, 3.68 g (27.2 m mole) of HOBT, and 3.72 g (27.2 m mole) of 4-pyridylacetic acid. The mixture was stirred at room temperature for 22 hours. The mixture was poured into 3300 mL of CH2Cl2 and washed with 500 mL of water. The aqueous layer was extracted with 500 mL of CH2Cl2. The combined organic portions were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography using a solution of 1.5% (10% NH4OH in MeOH) in CH2Cl2. The product was obtained as a white amorphous solid, M.S. (Mass Spec) M+=433.

Workup

  1. washwashed with 500 mL of water
  2. extractionThe aqueous layer was extracted with 500 mL of CH2Cl2
  3. dry with materialThe combined organic portions were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. customThe product was obtained as a white amorphous solid, M.S

Sources & evidence

ORD record
ord-7d5a845c7d344d979954bc8c8df9e622
Source dataset
uspto-grants-1997_12
Patent number
US05700806

Reaction notes

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