Acetyl chloride → (R)-1-Methoxy-3-(7-methyl-1H-indazol-5-yl)-1-oxopropan-2-yl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate

HRID 501954Notes

Reaction equation

HRID 501954 reaction equation
[O:1]=[C:2]1[C:11]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C@H:21]([CH2:26][C:27]3[CH:35]=[C:34]([CH3:36])[C:33]4[C:29](=[CH:30][N:31](COC)[N:32]=4)[CH:28]=3)[C:22]([O:24][CH3:25])=[O:23])=[O:19])[CH2:14][CH2:13]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.C(Cl)(=O)C>CO>[O:1]=[C:2]1[C:11]([CH:12]2[CH2:13][CH2:14][N:15]([C:18]([O:20][C@H:21]([CH2:26][C:27]3[CH:28]=[C:29]4[C:33](=[C:34]([CH3:36])[CH:35]=3)[NH:32][N:31]=[CH:30]4)[C:22]([O:24][CH3:25])=[O:23])=[O:19])[CH2:16][CH2:17]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 57794695(R)-1-Methoxy-3-(2-(methoxymethyl)-7-methyl-2H-indazol-5-yl)-1-oxopropan-2-yl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate

Product 1

HCID 59424336(R)-1-Methoxy-3-(7-methyl-1H-indazol-5-yl)-1-oxopropan-2-yl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-1-methoxy-3-(2-(methoxymethyl)-7-methyl-2H-indazol-5-yl)-1-oxopropan-2-yl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate (1.20 g, 2.25 mmol) in methanol (20 mL) was added acetyl chloride (0.40 mL, 5.62 mmol). The reaction was warmed to reflux and held there for 1 h. The reaction was concentrated by rotary evaporation under high vacuum and purified by column chromatography (5% methanol/dichloromethane) to give 1.09 g (99%) as a white foam solid. Mass spec.: 489.29 (MH)+.

Workup

  1. temperatureThe reaction was warmed
  2. temperatureto reflux
  3. concentrationThe reaction was concentrated by rotary evaporation under high vacuum
  4. custompurified by column chromatography (5% methanol/dichloromethane)
  5. customto give 1.09 g (99%) as a white foam solid

Sources & evidence

ORD record
ord-c91a73cdacb4409081013a6a3d2ed735
Source dataset
uspto-grants-2010_08
Patent number
US07772244B2

Reaction notes

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