Hydrochloric Acid → HCID 68459372, compound

HRID 2387498Notes

Reaction equation

HRID 2387498 reaction equation
[F:1][C:2]1[CH:32]=[CH:31][C:5](/[CH:6]=[CH:7]/[C:8]2[CH:13]=[CH:12][N:11]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[N:19]([CH2:23][CH2:24][N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[N:18]=[CH:17]4)[C:10](=[O:30])[CH:9]=2)=[CH:4][CH:3]=1.C([O-])=O.[NH4+].[ClH:37]>CO.[Pd].CCOCC>[ClH:37].[F:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][N:11]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[N:19]([CH2:23][CH2:24][N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[N:18]=[CH:17]4)[C:10](=[O:30])[CH:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 2723923Ammonium formateHCID 59293396HCID 59293396, compound

Product 1

HCID 68459372HCID 68459372, compoundYield 8.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

(E)-4-(4-Fluorostyryl)-1-(1-(2-(pyrrolidin-1-yl)ethyl)-1H-indazol-5-yl)pyridin-2(1H)-one (51 mg, 0.11 mmol) and ammonium formate (13.3 mg, 0.211 mmol) were stirred in methanol (4 ml) for 5 min. Palladium on carbon (100 mg) was added, and the mixture was heated to reflux for 1.5 h. The reaction mixture was cooled to room temperature, filtered through celite, rinsed with ethanol, and then concentrated. The residue was dissolved in methanol (2 mL) and treated with 1 equivalent of 2 M HCl in Et2O, and the mixture was concentrated to provide the title compound (42.3 mg, 8.5%) as a yellow solid. mp 200-210° C.; 1H NMR (500 MHz, CD3OD) δ 8.23 (s, 1H), 7.83 (s, 1H), 7.78 (d, J=8.8 Hz, 1H), 7.61-7.51 (m, 6H), 7.48-7.44 (dd, J=9.0, 2.0 Hz, 1H), 7.41 (t, J=7.6 Hz, 2H), 7.35-7.27 (m, 3H), 6.49-6.47 (m, 1H), 4.86 (t, J=57 Hz, 2H), 3.85 (t, J=57 Hz, 2H), 3.74-3.62 (br m, 2H), 3.20-3.11 (br m, 2H), 3.07-3.00 (m, 2H), 2.97-2.91 (br m, 2H), 2.19-2.11 (m, 2H), 2.05-1.96 (br m, 2H); ESI MS m/z 489 [M+H]+; HPLC (Method D)>92.7% (AUC), tR=14.8 min.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1.5 h
  3. filtrationfiltered through celite
  4. washrinsed with ethanol
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in methanol (2 mL)
  7. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-0f8d12227dc240b8a32ff709d9ce1a2f
Source dataset
uspto-grants-2012_09
Patent number
US08268868B2

Reaction notes

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