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Dichloromethane → HCID 9889061, compound

HRID 840268
Notes
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Reaction equation

HRID 840268 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.CN1CC[O:27][CH2:26][CH2:25]1.[CH:30]1[CH:31]=[CH:32][C:33]2N(O)N=[N:36][C:34]=2C=1.C(Cl)Cl>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:15]([N:16]3[CH2:17][CH2:18][N:19]([C:26](=[O:27])[CH2:25][C:32]4[CH:31]=[CH:30][N:36]=[CH:34][CH:33]=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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 5255691HCID 5255691, compound

Product 1

HCID 9889061HCID 9889061, compound

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

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-methylmorpholine, 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-pynidylacetic 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-cd2ea2d6e37d4c13a319f551ba416dda
Source dataset
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06365588B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes