Potassium Carbonate → HCID 59438566, compound

HRID 1641030Notes

Reaction equation

HRID 1641030 reaction equation
Cl.[CH:2]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14](=[O:24])[C:15]([NH:17][CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[O:16])=[CH:6]1)([CH3:4])[CH3:3].C([O-])([O-])=O.[K+].[K+].Br[CH2:32][CH2:33][NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38]>C(#N)C>[CH:2]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14](=[O:24])[C:15]([NH:17][CH:18]2[CH2:19][CH2:20][N:21]([CH2:32][CH2:33][NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:22][CH2:23]2)=[O:16])=[CH:6]1)([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 66739286HCID 66739286, compound

Product 1

HCID 59438566HCID 59438566, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

The title compound was prepared according to general procedure C described in Scheme 2. 2-(1-Isopropyl-1H-indol-3-yl)-2-oxo-N-(piperidin-4-yl)acetamide hydrochloride (200 mg, 0.64 mmol) was treated with acetonitrile (3 mL), K2CO3 (265 mg, 1.91 mmol), and tert-butyl 2-bromoethylcarbamate (266 mg, 1.28 mmol). The reaction mixture was stirred at 65° C. for 72 h and was then concentrated under reduced pressure. The crude material was purified by silica chromatography (Biotage, 0-5% MeOH/DCM, 30 min.) to provide the title compound as a brown oil. The material was further purified using reverse phase HPLC to provide the desired product as a pink solid TFA salt (132 mg, 45%).

Workup

  1. customThe title compound was prepared
  2. concentrationwas then concentrated under reduced pressure
  3. customThe crude material was purified by silica chromatography (Biotage, 0-5% MeOH/DCM, 30 min.)

Sources & evidence

ORD record
ord-65c5a462341943559e9b2b138a1ac8b1
Source dataset
uspto-grants-2012_02
Patent number
US08114894B2

Reaction notes

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