Butylamine → N-butyl-2-[(2'-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,3'-indol]-1'(2'H)-yl)methyl]benzamide
Reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].C1(CN)CCCCC1.[O:14]=[C:15]1[C:23]2([CH2:27][O:26][C:25]3[CH:28]=[C:29]4[C:33](=[CH:34][C:24]2=3)[CH2:32][CH2:31][O:30]4)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]1[CH2:35][C:36]1[CH:44]=[CH:43][CH:42]=[CH:41][C:37]=1[C:38](O)=[O:39].O=C1C2(COC3C=C4C(=CC2=3)CCO4)C2C(=CC=CC=2)N1CC1C=C(C=CC=1)C(O)=O>>[CH2:1]([NH:5][C:38](=[O:39])[C:37]1[CH:41]=[CH:42][CH:43]=[CH:44][C:36]=1[CH2:35][N:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:23]2([CH2:27][O:26][C:25]3[CH:28]=[C:29]4[C:33](=[CH:34][C:24]2=3)[CH2:32][CH2:31][O:30]4)[C:15]1=[O:14])[CH2:2][CH2:3][CH3:4]Participants
Reactant 4
Product 1
Procedure
Following the procedure as described in EXAMPLE 12 and making non-critical variations using butylamine to replace cyclohexanemethylamine, and 2-[(2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-1′(2′H)-yl)methyl]benzoic acid to replace 3-[(2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-1′(2′H)-yl)methyl]benzoic acid, N-butyl-2-[(2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-1′(2′H)-yl)methyl]benzamide was obtained (77%) as a colorless solid: mp 176-178° C.; 1H NMR (300 MHz, CDCl3) δ7.48-7.41 (m, 1H), 7.37-7.14 (m, 6H), 7.09-6.99 (m, 3H), 6.55-6.37 (m, 3H), 5.25-5.07 (m, 2H), 4.94 (d, J=9.0 Hz, 1H), 4.70 (d, J=9.0 Hz, 1H), 4.52 (t, J=8.2 Hz, 2H), 3.47 (q, J=6.6 Hz, 2H), 2.98 (t, J=8.7 Hz, 2H), 1.67-1.55 (m, 2H), 1.50-1.35 (m, 2H), 0.95 (t, J=6.6 Hz, 1H); MS (ES+) m/z 491.1 (M+23).
Sources & evidence
- ORD record
- ord-7eb3e7e8501a4c1cb85640b51a46687b
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415370B2
Reaction notes
Loading…