HCID 117635644, compound → HCID 117635649, compound

HRID 1481980Notes

Reaction equation

HRID 1481980 reaction equation
[CH3:1][C:2]1(C)[CH2:7][CH2:6][N:5]([C:8]2[N:13]3[CH:14]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:16]=[C:12]3[CH:11]=[C:10]([CH3:22])[C:9]=2[C@H:23]([OH:28])[C:24]([O:26][CH3:27])=[O:25])[CH2:4][CH2:3]1>C(Cl)Cl.C(OC(C)(C)C)(=O)C>[CH2:17]([O:18][C:2]1([CH3:1])[CH2:7][CH2:6][N:5]([C:8]2[N:13]3[CH:14]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:16]=[C:12]3[CH:11]=[C:10]([CH3:22])[C:9]=2[C@H:23]([O:28][C:2]([CH3:7])([CH3:3])[CH3:1])[C:24]([O:26][CH3:27])=[O:25])[CH2:4][CH2:3]1)[CH:15]=[CH2:14]

Participants

4

Reactant 1

HCID 117635644HCID 117635644, compound

Product 1

HCID 117635649HCID 117635649, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 10908tert-Butyl acetateSolvent

Procedure

(S)-Ethyl 5-(4,4-dimethylpiperidin-1-yl)-6-(1-hydroxy-2-methoxy-2-oxoethyl)-7-methylimidazo[1,2-a]pyridine-2-carboxylate (1.3 g, 3.22 mmol, 1 equiv) was suspended in DCM (3 mL) and tert-butyl acetate (10 mL). To this mixture was added 70% HClO4 (0.831 mL, 9.67 mmol, 3 equiv) through sealed rubber stopper. After 2 h, LCMS indicated about 60% conversion. The reaction was washed with 1 N NaOH, dried (Na2SO4), and concentrated in vacuo. The crude product was purified via silica gel flash chromatography (0-100% EtOAc [2% TEA]/hexane) to provide the product (0.68 g, 46%). 1H NMR (400 MHz, CDCl3) 8.22 (d, J=0.8 Hz, 1H), 7.31 (s, 1H), 6.02 (s, 1H), 4.47 (q, J=7.2 Hz, 2H), 3.70 (s, 3H), 3.60 (td, J=11.4, 2.8 Hz, 1H), 3.49 (td, J=11.5, 2.6 Hz, 1H), 3.10 (dt, J=11.9, 3.5 Hz, 1H), 2.95-2.86 (m, 1H), 2.44 (d, J=1.0 Hz, 3H), 1.73-1.48 (m, 7H), 1.45 (t, J=7.0 Hz, 4H), 1.24 (s, 10H), 1.15 (s, 3H), 1.08 (s, 3H); LCMS (ESI, M+1): 502.35.

Workup

  1. customthrough sealed rubber stopper
  2. washThe reaction was washed with 1 N NaOH
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified via silica gel flash chromatography (0-100% EtOAc [2% TEA]/hexane)

Sources & evidence

ORD record
ord-3b8b70c388704ae990a9d881866acc60
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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