4-Methylmorpholine → 5-Chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid (2-oxo-2-phenylethyl)amide

HRID 1693488Notes

Reaction equation

HRID 1693488 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=[N:6][CH:7]=1.Cl.[NH2:15][CH2:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:18].C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-].CN1CCOCC1>C1COCC1>[O:18]=[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:16][NH:15][C:11]([C:9]1[NH:8][C:5]2=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=[C:4]2[CH:10]=1)=[O:13]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 2723597Ethanone, 2-amino-1-phenyl-, hydrochloride (1:1)HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 446307055-chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid

Product 1

HCID 112207335-Chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid (2-oxo-2-phenylethyl)amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid (Preparation 57, 50 mg, 0.25 mmol), 2-aminoacetophenone hydrochloride (48 mg, 0.28 mmol) and DMTMM (85 mg, 0.31 mmol) were dissolved in THF (5 mL) and 4-methylmorpholine (31 μL, 0.28 mmol). The reaction mixture was stirred at rt for 16 h. The solvent was removed in vacuo and the residue partitioned between water (20 mL) and EtOAc (3×20 mL). The combined organics were dried (MgSO4), concentrated in vacuo and purified by chromatography on silica gel eluting with methanol:dichloromethane (1:19) to give the title compound. m/z (ES+)=314 [M+H]+; RT=3.47 min.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between water (20 mL) and EtOAc (3×20 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)

Sources & evidence

ORD record
ord-b944fa97de8941f9987626fdb29a815a
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

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