HCID 75110103, compound → HCID 59352754, compound

HRID 1965682Notes

Reaction equation

HRID 1965682 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]1([C:25]3=[CH:26][C:27]4[O:31][CH2:30][O:29][C:28]=4[CH:32]=[C:24]3[O:23][CH2:22]1)[C:5](=[O:21])[N:6]2[CH2:11][C:12](=[N:14][O:15][C:16]([CH:18]1[CH2:20][CH2:19]1)=O)[NH2:13]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]1([C:25]3=[CH:26][C:27]4[O:31][CH2:30][O:29][C:28]=4[CH:32]=[C:24]3[O:23][CH2:22]1)[C:5](=[O:21])[N:6]2[CH2:11][C:12]1[N:13]=[C:16]([CH:18]2[CH2:19][CH2:20]2)[O:15][N:14]=1

Participants

3

Reactant 1

HCID 75110103HCID 75110103, compound

Product 1

HCID 59352754HCID 59352754, compoundYield 158.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A stirred solution of 2-(4′-chloro-2′-oxospiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-1′(2′H)-yl)-N′-[(cyclopropylcarbonyl)oxy]ethanimidamide (0.24 g, 0.52 mmol) in pyridine (1 mL) was heated at 170° C. for 30 min in a microwave reactor. The solution was concentrated in vacuo to dryness, purified by flash chromatography with ethyl acetate in hexanes (15% to 50% gradient) to afford 4′-chloro-1′-[(5-cyclopropyl-1,2,4-oxadiazol-3-yl)methyl]spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one (0.36 g, 16%) as a colorless solid: mp 180-182° C.; 1H NMR (300 MHz, CDCl3) δ7.19 (dd, J=8.1, 8.1 Hz, 1H), 6.99 (d, J=8.4 Hz, 1H), 6.77 (d, J=7.8 Hz, 1H), 6.46 (s, 1H), 6.28 (s, 1H), 5.86 (d, J=1.2 Hz, 1H), 5.04 (ABq, 2H), 4.94 (ABq, 2H), 2.20-2.10 (m, 1H). 1.26-1.12 (m, 4H); 13C NMR (75 MHz, CDCl3) δ182.9, 177.0, 165.4, 156.8, 149.2, 143.0, 142.1, 131.6, 130.0, 128.4, 124.6, 116.5, 107.4, 103.0, 101.5, 93.2, 58.7, 36.1, 10.57, 10.53, 7.8; MS (ES+) m/z 438.1 (M+1).

Workup

  1. concentrationThe solution was concentrated in vacuo to dryness
  2. custompurified by flash chromatography with ethyl acetate in hexanes (15% to 50% gradient)

Sources & evidence

ORD record
ord-04ea8456f5dc44dfa0dbb5a52c0d2f25
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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