HCID 58303860, compound → HCID 58303981, compound

HRID 1404107Notes

Reaction equation

HRID 1404107 reaction equation
[Si](OCCC1C2C(O)=C(F)C=CC=2N(C)C=1)(C(C)(C)C)(C)C.[N:23]([CH2:26][CH2:27][C:28]1[C:36]2[C:31](=[CH:32][CH:33]=[C:34]([F:45])[C:35]=2[O:37]CC2C=CC=CC=2)[N:30]([CH2:46][CH:47]2[CH2:52][CH2:51][CH2:50][CH2:49][O:48]2)[CH:29]=1)=[N+]=[N-]>[OH-].[OH-].[Pd+2].[Pd]>[NH2:23][CH2:26][CH2:27][C:28]1[C:36]2[C:35]([OH:37])=[C:34]([F:45])[CH:33]=[CH:32][C:31]=2[N:30]([CH2:46][CH:47]2[CH2:52][CH2:51][CH2:50][CH2:49][O:48]2)[CH:29]=1

Participants

5

Reactant 2

HCID 58303860HCID 58303860, compoundHCID 58303876HCID 58303876, compound

Product 1

HCID 58303981HCID 58303981, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 9942167Palladium hydroxideCatalyst

Procedure

Following the procedure (step 4, scheme 17) used to prepare compound 17-5, compound 19-2 was used as starting material, using Pd(OH)2/C (20%) as source of Pd to afford 19-3 (45% yield) as a white solid. The compound was then converted to the hydrochloride salt. 1H NMR (D2O, 300 MHz) δ (ppm) (HCl salt): 7.06 (s, 1H), 7.03 (dd, J=11.2, 9.1 Hz, 1H), 6.89 (dd, J=9.1, 3.6 Hz, 1H), 4.10 (dd, J=15.1, 4.1 Hz, 1H), 4.04 (dd, J=15.1, 7.7 Hz, 1H), 3.75-3.84 (m, 2H), 3.27-3.36 (m, 3H), 3.12-3.17 (m, 2H), 1.63-1.79 (m, 2H), 1.40-1.50 (m, 3H), 1.20-1.28 (m, 1H). LRMS: calc 292.2 found 293.1 [MH]+.

Sources & evidence

ORD record
ord-c56c8a9019aa44ae86674c6918837c5a
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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