4-Methylmorpholine → HCID 57550107, compound

HRID 751706Notes

Reaction equation

HRID 751706 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([C:11]([OH:13])=O)[NH:8][C:5]2=[CH:6][N:7]=1.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.Cl.[CH2:33]([O:35][C:36](=[O:47])[CH:37]([NH2:46])[C:38](=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH3:34].CN1CCOCC1>C1COCC1>[CH2:33]([O:35][C:36](=[O:47])[CH:37]([NH:46][C:11]([C:9]1[NH:8][C:5]2=[CH:6][N:7]=[C:2]([Cl:1])[CH:3]=[C:4]2[CH:10]=1)=[O:13])[C:38](=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH3:34]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 24193015107438-51-7HCID 446307045-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid

Product 1

HCID 57550107HCID 57550107, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (100 mg, 0.51 mmol) and 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride (DMTMM) (183 mg, 0.66 mmol) were dissolved in THF (20 ml). After 5 min, 2-amino-3-oxo-3-phenylpropionic acid ethyl ester hydrochloride (Tetrahedron Lett., 1993, 34(2), 211–214; 124 mg, 0.51 mmol) and 4-methylmorpholine (56 μl, 0.51 mmol) were added and the reaction mixture stirred at rt for 72 h. The solvent was removed in vacuo and the residue partitioned between water (40 ml) and EtOAc (3×30 ml). The combined organics were dried (MgSO4), concentrated in vacuo and purified by chromatography on silica gel eluting with methanol:dichloromethane (1:19). This material was further triturated with methanol:diethyl ether (1:19) to give the title compound as a pale yellow solid. m/z (ES+)=386 [M+H]+; RT=3.56 min.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between water (40 ml) and EtOAc (3×30 ml)
  3. dry with materialThe combined organics were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by chromatography on silica gel eluting with methanol:dichloromethane (1:19)
  6. customThis material was further triturated with methanol:diethyl ether (1:19)

Sources & evidence

ORD record
ord-8bbfb8d492db4c6886c31138a983ec69
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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