4-Methylmorpholine → HCID 57980172, compound

HRID 1867796Notes

Reaction equation

HRID 1867796 reaction equation
[Na+].[C:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:19]=[CH:18][C:14]([C:15]([O-:17])=O)=[CH:13][CH:12]=2)=[N:9][CH:10]=1)(=[O:4])[CH3:3].CN1CCOCC1.ClC1N=C(OC)N=C(OC)N=1.[NH:38]1[CH2:42][CH2:41][CH2:40][C@H:39]1[CH2:43][N:44]1[CH2:48][CH2:47][CH2:46][CH2:45]1>ClCCl>[N:44]1([CH2:43][C@@H:39]2[CH2:40][CH2:41][CH2:42][N:38]2[C:15]([C:14]2[CH:13]=[CH:12][C:11]([C:8]3[N:9]=[CH:10][C:5]([C:2](=[O:4])[CH3:3])=[CH:6][CH:7]=3)=[CH:19][CH:18]=2)=[O:17])[CH2:48][CH2:47][CH2:46][CH2:45]1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 853152(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidineHCID 67371312HCID 67371312, compound

Product 1

HCID 57980172HCID 57980172, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Procedure W′: To a stirring solution of 4-(5-acetyl-pyridin-2-yl)-benzoic acid sodium salt (11.0 mmol) and n-methyl morpholine (1.0 mmol) in dichloromethane (0.10M) in a 0° C. ice bath, add 2-chloro-4,6-dimethoxy-1,3,5-triazine (1.0 mmol). Remove the ice bath and stir for 45 minutes. After this time, add (S)-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine (1.0 mmol) and stir at room temperature for three hours. After this time, wash the reaction with saturated aqueous sodium bicarbonate while extracting with 10% isopropanol/dichloromethane (3×). Dry the organic layer with sodium sulfate, filter and concentrate in vacuo. Purify the title compound via chromatography eluting with 2M ammonia in methanol and dichloromethane. MS (m/e): 378.3 (M+1)

Workup

  1. customRemove the ice bath
  2. stirringstir at room temperature for three hours
  3. washAfter this time, wash
  4. customthe reaction with saturated aqueous sodium bicarbonate
  5. extractionwhile extracting with 10% isopropanol/dichloromethane (3×)
  6. dry with materialDry the organic layer with sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. customPurify the title compound via chromatography
  10. washeluting with 2M ammonia in methanol and dichloromethane

Sources & evidence

ORD record
ord-e4b503ac839c490f9b57e80b4d08e8e8
Source dataset
uspto-grants-2009_12
Patent number
US07632857B2

Reaction notes

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