Pyridine → HCID 59464262, compound

HRID 1713893Notes

Reaction equation

HRID 1713893 reaction equation
N1C=CC=CC=1.Cl[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].[Cl:18][C:19]1[CH:25]=[C:24]([CH:26]2[CH2:35][CH2:34][C:29]3([O:33][CH2:32][CH2:31][O:30]3)[CH2:28][CH2:27]2)[CH:23]=[CH:22][C:20]=1[NH2:21].C(OCC)(=O)C>C1COCC1>[Cl:18][C:19]1[CH:25]=[C:24]([CH:26]2[CH2:35][CH2:34][C:29]3([O:30][CH2:31][CH2:32][O:33]3)[CH2:28][CH2:27]2)[CH:23]=[CH:22][C:20]=1[NH:21][C:8](=[O:9])[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 59464341HCID 59464341, compound

Product 1

HCID 59464262HCID 59464262, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Pyridine (2.18 mL, 26.9 mmol) and benzyl chloroformate (1.53 g, 8.96 mmol) were added sequentially, each in one portion, to a stirred solution of 2-chloro-4-(1,4-dioxaspiro[4.5]dec-8-yl)aniline (2.40 g, 8.96 mmol) in THF (30 mL) at 5° C. and the reaction mixture was stirred at 10° C. for 3 h. Ethyl acetate (75 mL) was added and the mixture was washed with H2O (2×30 mL) and brine. The organic layer was dried (MgSO4) and concentrated in vacuo to leave a solid, which was purified by column chromatography, using a gradient of 20-50% ethyl acetate:isohexane as eluent, to give the title compound (2.6 g, 72%) as a white solid; 1H NMR δ 1.65-1.93 (8H, m), 2.49-2.6 (1H, m), 4.0 (4H, s), 5.25 (2H, s), 7.12 (1H, s), 7.15 (1H, dd), 7.25 (1H, d), 7.37-7.48 (5H, m), 8.08 (1H, d); MS m/e (M−H)− 400.

Workup

  1. washthe mixture was washed with H2O (2×30 mL) and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customto leave a solid, which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-e44bc9715380428ba69054d39838773c
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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