Reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]2([C:16]3=[CH:17][C:18]4[O:22][CH2:21][O:20][C:19]=4[CH:23]=[C:15]3[O:14][CH2:13]2)[C:5]1=[O:24].NCCCN1C2C(=CC=CC=2)C2(C3=CC4OCOC=4C=C3OC2)C1=O.[F:50][C:51]([F:63])([F:62])[O:52][C:53]1[CH:61]=[CH:60][CH:59]=[CH:58][C:54]=1[C:55](Cl)=[O:56].ClC1C=CSC=1C(Cl)=O>>[O:24]=[C:5]1[C:6]2([C:16]3=[CH:17][C:18]4[O:22][CH2:21][O:20][C:19]=4[CH:23]=[C:15]3[O:14][CH2:13]2)[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]1[CH2:3][CH2:2][NH:1][C:55](=[O:56])[C:54]1[CH:58]=[CH:59][CH:60]=[CH:61][C:53]=1[O:52][C:51]([F:50])([F:62])[F:63]Participants
Reactant 4
Product 1
Procedure
Following the procedure as described in EXAMPLE 17, and making non-critical variations using 1′-(2-aminoethyl)spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one to replace 1′-(3-aminopropyl)spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one, and 2-(trifluoromethoxy)benzoyl chloride to replace 3-chlorothiophene-2-carbonyl chloride, the title compound was obtained (91%) as a colorless solid: mp 183-184° C.; 1H NMR (300 MHz, CDCl3) δ 7.86-7.83 (m, 1H), 7.50-7.45 (m, 1H), 7.37-7.27 (m, 3H), 7.16-7.11 (m, 2H), 7.07-7.02 (m, 1H), 6.84 (t, 1H), 6.47 (s, 1H), 6.10 (s, 1H), 5.82 (dd, 2H), 4.87 (d, 1H), 4.64 (d, 1H), 4.10-3.94 (m, 2H), 3.90-3.68 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 178.2, 165.0, 155.9, 148.8, 145.9, 142.3, 141.9, 132.4, 132.1, 131.3, 129.2, 127.6, 127.3, 124.0, 123.6, 121.2, 121.1, 119.2, 108.7, 103.0, 101.4, 93.6, 80.4, 58.2, 39.5, 38.2; MS (ES+) m/z 513.4 (M+1).
Sources & evidence
- ORD record
- ord-1d69387f05454259936763eedaedd509
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08106087B2
Linked notes
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