Dimethylformamide → HCID 67060238, compound

HRID 1625107Notes

Reaction equation

HRID 1625107 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16](=[O:17])[CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15][N:10]3[C:9]2=[O:18])=[C:4]([O:19][CH3:20])[CH:3]=1.CCN(C(C)C)C(C)C.Cl.[N:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH2:37]Cl.CN(C=[O:43])C>>[O:17]=[C:16]1[CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][N:10]2[C:9](=[O:18])[N:8]1[C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:37](=[O:43])[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][N:31]=2)=[CH:3][C:4]=1[O:19][CH3:20]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 23392Picolyl chloride hydrochlorideHCID 81531DiisopropylethylamineHCID 67060294HCID 67060294, compound

Product 1

HCID 67060238HCID 67060238, compound

Conditions

Temperature
50 °C

Procedure

To a mixture of 2-(4-amino-2-methoxyphenyl)tetrahydroimidazo[1,5-a]pyridine-1,3(2H,5H)-dione (250 mg; 0.908 mmol) in DMF (5 mL) was added DIEA (316 μL; 1.82 mmol) followed by picolinyl chloride HCl (194 mg; 1.09 mmol). The reaction mixture was stirred at 50° C. overnight and then cooled to rt and washed with CH2Cl2 and H2O. The organic layer was concentrated and purified by flash column chromatography (EtOAc) yielding N-(4-(1,3-dioxotetrahydroimidazo[1,5-a]pyridin-2(1H,3H,5H)-yl)-3-methoxyphenyl)picolinamide, 1.3.1.

Workup

  1. temperaturecooled to rt
  2. washwashed with CH2Cl2 and H2O
  3. concentrationThe organic layer was concentrated
  4. custompurified by flash column chromatography (EtOAc)

Sources & evidence

ORD record
ord-d1184591ad0b441095f6022777e2f26a
Source dataset
uspto-grants-2014_07
Patent number
US08779157B2

Reaction notes

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