4-Methylmorpholine → HCID 178519434, compound

HRID 646437Notes

Reaction equation

HRID 646437 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[CH2:6][N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.CN1CCOCC1.[Cl:19][C:20]1[CH:37]=[CH:36][C:23]2[NH:24][C:25]([C:27]3[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=3)=[N:26][C:22]=2[CH:21]=1>ClCCl>[Cl:19][C:20]1[CH:37]=[CH:36][C:23]2[NH:24][C:25]([C:27]3[CH:28]=[CH:29][C:30]([C:31]([N:1]4[CH2:5][CH2:4][CH2:3][CH:2]4[CH2:6][N:7]4[CH2:11][CH2:10][CH2:9][CH2:8]4)=[O:32])=[CH:34][CH:35]=3)=[N:26][C:22]=2[CH:21]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 853152(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidineHCID 178521105HCID 178521105, compound

Product 1

HCID 178519434HCID 178519434, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of (S)-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine (11.0 mmol) and n-methylmorpholine (1.0 mmol) in dichloromethane (0.10M), slowly add the product from 4-(5-Chloro-1H-benzoimidazol-2-yl)-benzoyl chloride (1.0 mmol) diluted in dichloromethane. Stir reaction at room temperature for two hours. After this time wash the reaction with saturated aqueous sodium bicarbonate while extracting with 10% isopropanol/dichloromethane. Concentrate the organics in vacuo. Purify via radial chromatography eluting with 2M ammonia in methanol and dichloromethane. MS (m/e): 409.3 (M+1)

Workup

  1. customreaction at room temperature for two hours
  2. washAfter this time wash
  3. customthe reaction with saturated aqueous sodium bicarbonate
  4. extractionwhile extracting with 10% isopropanol/dichloromethane
  5. concentrationConcentrate the organics in vacuo
  6. customPurify via radial chromatography
  7. washeluting with 2M ammonia in methanol and dichloromethane

Sources & evidence

ORD record
ord-c7abed03c2794a7f875580b3e9fc9013
Source dataset
uspto-grants-2010_04
Patent number
US07705025B2

Reaction notes

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