HCID 90403814, compound → HCID 90403357, compound

HRID 589809Notes

Reaction equation

HRID 589809 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)=[O:10])=[CH:4][C:3]=1[C:16]1[O:17][C:18]2[C:19]([N:26]=1)=[N:20][CH:21]=[C:22]([CH:24]=[CH2:25])[CH:23]=2>CCOC(C)=O.ClCCl.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)=[O:10])=[CH:4][C:3]=1[C:16]1[O:17][C:18]2[C:19]([N:26]=1)=[N:20][CH:21]=[C:22]([CH2:24][CH3:25])[CH:23]=2

Participants

4

Reactant 1

HCID 90403814HCID 90403814, compound

Product 1

HCID 90403357HCID 90403357, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21226138Dichloromethane ethylacetateSolvent

Procedure

N-(4-chloro-3-(6-vinyloxazolo[4,5-b]pyridin-2-yl)phenyl)-furan-2-carboxamide (I-22) was dissolved in EtOAc/dichloromethane (1:1; 12 ml). To the solution, catalytic amount of 5 wt % Pd—C was added. The reaction was stirred under hydrogen atmosphere for 30 minutes. LCMS indicated that the reaction was complete with a formation of new peak of desired mass 368.1 (M+1). The reaction was filtered to remove palladium on carbon and the filterate wasn concentrated under reduced pressure. The crude product was purified by column chromatography to yield the desired product N-(4-chloro-3-(6-ethyloxazolo[4,5-b]pyridin-2-yl)phenyl)furan-2-carboxamide (Example 419). 1H NMR (400 MHz, DMSO) δ 10.63 (s, 1H), 8.73 (d, J=2.6 Hz, 1H), 8.51 (d, J=1.8 Hz, 1H), 8.21 (d, J=1.5 Hz, 1H), 8.12-8.03 (m, 1H), 8.00 (dd, J=6.3, 7.0 Hz, 1H), 7.74 (t, J=10.6 Hz, 1H), 7.46-7.38 (m, 1H), 6.75 (dd, J=1.7, 3.5 Hz, 1H), 2.83 (q, J=7.6, 2H), 1.34-1.22 (m, 3H). LCMS M/Z=368.1 (M+1). RT=3.20: Method A.

Workup

  1. filtrationThe reaction was filtered
  2. customto remove palladium on carbon
  3. concentrationthe filterate wasn concentrated under reduced pressure
  4. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-b6fa0b3afb7d4a89aad58e46bdb15d7f
Source dataset
uspto-grants-2016_01
Patent number
US09233961B2

Reaction notes

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