Acetic acid methanol → HCID 59129257, compound

HRID 1404056Notes

Reaction equation

HRID 1404056 reaction equation
[N:1]([CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:16]([C:18]3([C:21]4[CH:29]=[CH:28][C:24]5[O:25][CH2:26][O:27][C:23]=5[CH:22]=4)[CH2:20][CH2:19]3)=[O:17])=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:30]([CH3:33])([CH3:32])[CH3:31])=[N+]=[N-].CO.[CH3:36][C:37](O)=[O:38]>[Pd]>[C:37]([NH:1][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:16]([C:18]3([C:21]4[CH:29]=[CH:28][C:24]5[O:25][CH2:26][O:27][C:23]=5[CH:22]=4)[CH2:20][CH2:19]3)=[O:17])=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:30]([CH3:33])([CH3:32])[CH3:31])(=[O:38])[CH3:36]

Participants

4

Reactant 2

HCID 10129899Acetic acid methanolHCID 59129277HCID 59129277, compound

Product 1

HCID 59129257HCID 59129257, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of N-(1-(2-azidoethyl)-2-tert-butyl-1H-indol-5-yl)-1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (13 mg, 0.029 mmol) in MeOH-AcOH (0.2 mL, 99:1) in the presence of Pd—C (2 mg) was stirred at room temperature under 1 atm of H2 for 2 h, filtered through Celite, and concentrated under reduced pressure. The crude product was treated with AcCl (0.05 mL) and Et3N (0.05 mL) in anhydrous THF (0.2 mL) at 0° C. for 30 min and then 1 h at room temperature. The mixture was purified by preparative HPLC providing N-(1-(2-acetamidoethyl)-2-tert-butyl-1H-indol-5-yl)-1-(benzo[d][1,3]-dioxol-5-yl)cyclopropanecarboxamide. MS (ESI) m/e (M+H+) 462.0.

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated under reduced pressure
  3. additionThe crude product was treated with AcCl (0.05 mL) and Et3N (0.05 mL) in anhydrous THF (0.2 mL) at 0° C. for 30 min
  4. custom1 h
  5. customat room temperature
  6. customThe mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-35916280aa9248f5b431e2ea55fd5437
Source dataset
uspto-grants-2014_12
Patent number
US08912199B2

Reaction notes

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