Methanol → HCID 86761341, compound

HRID 2425752Notes

Reaction equation

HRID 2425752 reaction equation
[CH:1]([N:4]1[C:13]2[C:8](=[C:9]([CH3:14])[CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]([C:15]([NH:17][CH2:18][CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[O:16])[C:5]1=[O:25])([CH3:3])[CH3:2].[O:26]1[C:28]2([CH2:33][CH2:32][N:31]([C:34]([O:36]C(C)(C)C)=[O:35])[CH2:30][CH2:29]2)[CH2:27]1.[CH3:41][OH:42]>>[C:34]([OH:36])(=[O:35])[C:41]([OH:16])=[O:42].[OH:26][C:28]1([CH2:27][N:22]2[CH2:23][CH2:24][CH:19]([CH2:18][NH:17][C:15]([C:6]3[C:5](=[O:25])[N:4]([CH:1]([CH3:3])[CH3:2])[C:13]4[C:8]([CH:7]=3)=[C:9]([CH3:14])[CH:10]=[CH:11][CH:12]=4)=[O:16])[CH2:20][CH2:21]2)[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1

Participants

4

Reactant 3

HCID 887MethanolHCID 22135564tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylateHCID 59822470HCID 59822470, compound

Product 1

HCID 86761341HCID 86761341, compoundYield 45%

Procedure

A solution of 1-isopropyl-5-methyl-2-oxo-N-(piperidin-4-ylmethyl)-1,2-dihydroquinoline-3-carboxamide (150 mg, 0.44 mmol, step 4 in preparation 3) and tert-butyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate (112 mg, 0.53 mmol, Castro Jose L. et al., J. Med. Chem., 1998, 41, 2667) in methanol (5 mL) was heated at 80° C. overnight. After cooled to room temperature, concentrated gave yellow oil. The residue was chromatographed on a column of silica gel eluting with 25% ammonium hydroxide/methanol/dichloromethane (2/10/100) to give 111 mg (45%) of the title compound as a white solid.

Workup

  1. concentrationconcentrated
  2. customgave yellow oil
  3. customThe residue was chromatographed on a column of silica gel eluting with 25% ammonium hydroxide/methanol/dichloromethane (2/10/100)

Sources & evidence

ORD record
ord-fb44c75cc00d4a618ebd8a9d70bbf593
Source dataset
uspto-grants-2011_06
Patent number
US07964727B2

Reaction notes

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