3,3-Dimethylbutylamine → N-methyl-5-[(2'-oxospiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-1'(2'H)-yl)methyl]-2-(trifluoromethyl)furan-3-carboxamide
Reaction equation
Cl.CN.CC(C)(C)C[CH2:7][NH2:8].O=[C:12]1[O:16][C:15]2[CH:17]=[C:18]3[O:44][CH2:43][C:21]4([C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[N:23]([CH2:30][C:31]5[O:35][C:34]([C:36]([F:39])([F:38])[F:37])=[C:33]([C:40]([OH:42])=O)[CH:32]=5)[CH2:22]4)[C:19]3=[CH:20][C:14]=2[O:13]1.[O:45]=C1C2(COC3C=C4C(=CC2=3)CCO4)C2C(=CC=CC=2)N1CC(O)=O>>[CH3:7][NH:8][C:40]([C:33]1[CH:32]=[C:31]([CH2:30][N:23]2[C:24]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:21]3([C:19]4=[CH:20][C:14]5[O:13][CH2:12][O:16][C:15]=5[CH:17]=[C:18]4[O:44][CH2:43]3)[C:22]2=[O:45])[O:35][C:34]=1[C:36]([F:39])([F:37])[F:38])=[O:42]Participants
Reactant 4
Product 1
Procedure
Following the procedure as described in EXAMPLE 12.49 and making non-critical variations using methylamine hydrochloride to replace 3,3-dimethylbutylamine, 5-[(2-oxospiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-1′(2′H)-yl)methyl]-2-(trifluoromethyl)furan-3-carboxylic acid to replace (2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-1′(2′H)-yl)acetic acid, N-methyl-5-[(2′-oxospiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-1′(2′H)-yl)methyl]-2-(trifluoromethyl)furan-3-carboxamide was obtained (96%) as a colorless solid: mp 202-203° C. (diethyl ether/hexanes); 1H NMR (300 MHz, CDCl3) 7.31-7.27 (m, 2H), 7.19-7.17 (m, 1H), 7.10-7.05 (m, 1H), 6.95-6.92 (m, 1H), 6.62 (s, 1H), 6.49 (s, 1H), 6.09 (s, 1H), 5.94 (br s, 1H), 5.85-5.84 (m, 2H), 5.03-4.85 (m, 3H), 4.67-4.64 (m, 1H), 2.92 (d, J=3.0 Hz, 3H); MS (ES+) m/z 487.3 (M+1).
Sources & evidence
- ORD record
- ord-2c49011e0f8c4417b776c6bf8b2be491
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08263606B2
Reaction notes
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