Acetyl chloride → HCID 59352619, compound

HRID 1407816Notes

Reaction equation

HRID 1407816 reaction equation
[OH:1][N:2]=[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]3([CH2:24][O:23][C:22]4[CH:25]=[C:26]5[C:30](=[CH:31][C:21]3=4)[CH2:29][CH2:28][O:27]5)[C:13]2=[O:32])[CH:6]=1)[NH2:4].[C:33](Cl)(=O)[CH3:34]>N1C=CC=CC=1>[CH3:33][C:34]1[O:1][N:2]=[C:3]([C:5]2[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=2)[CH2:11][N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]3([CH2:24][O:23][C:22]4[CH:25]=[C:26]5[C:30](=[CH:31][C:21]3=4)[CH2:29][CH2:28][O:27]5)[C:13]2=[O:32])[N:4]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 76748362HCID 76748362, compound

Product 1

HCID 59352619HCID 59352619, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
170 °C

Procedure

To a solution of N′-hydroxy-3-[(2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-1′(2′H)-yl)methyl]benzenecarboximidamide (0.36 g, 0.84 mmol) in pyridine (3 mL) was added acetyl chloride (0.12 mL, 1.68 mmol). The reaction was stirred in a microwave reactor (170° C., 200 watts, 200 psi) for 30 min. The mixture was concentrated in vacuo. The residue was purified by column chromatography with ethyl acetate in hexanes (25% to 40% gradient), and recrystallized from ethyl acetate and diethylether to afford 1′-[3-(5-methyl-1,2,4-oxadiazol-3-yl)benzyl]-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one (0.27 g, 71%) as a colorless solid: mp 209-213° C.; 1H NMR (300 MHz, CDCl3) δ8.06-8.03 (m, 1H), 7.99-7.96 (m, 1H), 7.48-7.44 (m, 2H), 7.19-7.12 (m, 2H), 7.03-6.98 (m, 1H), 6.77-6.74 (m, 1H), 6.58 (s, 1H), 6.42 (s, 1H), 5.18 (d, J=15.8 Hz, 1H), 5.00 (d, J=9.0 Hz, 1H), 4.85 (d, J=15.8 Hz, 1H), 4.72 (d, J=9.0 Hz, 1H), 4.56-4.50 (m, 2H), 3.07-2.95 (m, 2H), 2.63 (s, 3H); 13C NMR (75 MHz, CDCl3) δ178.0, 176.7, 168.1, 161.9, 161.3, 141.9, 136.6, 132.8, 129.9, 129.6, 128.8, 127.5, 126.9, 126.0, 124.0, 123.6, 120.2, 120.1, 119.1, 109.2, 93.2, 80.6, 72.4, 57.8, 43.8, 29.1, 12.4; MS (ES+) m/z 451.8 (M+1).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe residue was purified by column chromatography with ethyl acetate in hexanes (25% to 40% gradient)
  3. customrecrystallized from ethyl acetate and diethylether

Sources & evidence

ORD record
ord-839f253a26f04bc28f215dab152d303d
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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