Methanol → HCID 86703285, compound

HRID 2409967Notes

Reaction equation

HRID 2409967 reaction equation
COC1[CH:11]=[C:10]2C([C:7]([CH2:18][C:19]3[N:24]=[C:23]([C:25]([O:27]C)=O)[CH:22]=[CH:21][CH:20]=3)=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:9]2)=CC=1.O.[NH2:30][NH2:31].[CH3:32]O.[O:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1>>[CH3:32][O:34][C:38]1[CH:11]=[C:10]2[C:35]([C:7]([CH2:18][C:19]3[N:24]=[C:23]([C:25]([NH:30][NH2:31])=[O:27])[CH:22]=[CH:21][CH:20]=3)=[C:8]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:9]2)=[CH:36][CH:37]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)HCID 50903302HCID 50903302, compound

Product 1

HCID 86703285HCID 86703285, compound

Procedure

A mixture of methyl 6-(6-methoxy-2-phenyl-1H-indol-3-ylmethyl)pyridine-2-carboxylate (300 mg), hydrazine monohydrate (0.4 mL), methanol (6 mL), and tetrahydrofuran (2 mL) was stirred at room temperature overnight. The precipitate was collected by filtration, washed with methanol, and then dried under reduced pressure to obtain the title compound (258 mg). 1H-NMR (DMSO-d6) δ ppm: 3.77 (3H, s), 4.38 (2H, s), 4.58 (2H, d, J=4.8 Hz), 6.63 (1H, dd, J=2.3, 8.7 Hz), 6.87 (1H, d, J=2.3 Hz), 7.21 (1H, dd, J=1.8, 7.0 Hz), 7.30-7.39 (2H, m), 7.43-7.53 (2H, m), 7.61-7.70 (2H, m), 7.73-7.83 (2H, m), 9.47-9.58 (1H, m), 11.20 (1H, s).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with methanol
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-1aee79bd31794bb29d72bab3de38632f
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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