Diisopropylethylamine → HCID 67060231, compound

HRID 1625108Notes

Reaction equation

HRID 1625108 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]([Cl:19])[CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[F:53][C:54]1[CH:59]=[CH:58][CH:57]=[C:56]([C:60](O)=[O:61])[N:55]=1>CN(C=O)C.O>[Cl:19][C:4]1[CH:3]=[C:2]([NH:1][C:60](=[O:61])[C:56]2[CH:57]=[CH:58][CH:59]=[C:54]([F:53])[N:55]=2)[CH:7]=[CH:6][C:5]=1[N:8]1[C:16](=[O:17])[CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][N:10]2[C:9]1=[O:18]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2260276-Fluoropyridine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67060278HCID 67060278, compound

Product 1

HCID 67060231HCID 67060231, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-(4-amino-2-chlorophenyl)tetrahydroimidazo[1,5-α]pyridine-1,3(2H,5H)-dione (0.03 g, 0.107 mmol), HATU (0.045 g, 0.119 mmol), DIEA (0.041 mL, 0.236 mmol) in DMF (1 mL) was added 2-fluoro-6-pyridine carboxylic acid (0.017 g, 0.118 mmol). The reaction mixture was stirred at room temperature for 15 h. The reaction was diluted with water (4 mL) and extracted with ethyl acetate (2×3 mL). The organic extracts were combined and concentrated. The residue was purified by reverse phase HPLC to give N-(3-chloro-4-(1,3-dioxotetrahydroimidazo[1,5-a]pyridin-2(1H,3H,5H)-yl)phenyl)-6-fluoropicolinamide (TFA), 1.3.4.

Workup

  1. extractionextracted with ethyl acetate (2×3 mL)
  2. concentrationconcentrated
  3. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-9342a9d9dd384421bf76f77111413cbb
Source dataset
uspto-grants-2014_07
Patent number
US08779157B2

Reaction notes

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