Ammonia → 5-[(2'-oxospiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-1'(2'H)-yl)methyl]-2-(trifluoromethyl)furan-3-carboxamide

HRID 1965756Notes

Reaction equation

HRID 1965756 reaction equation
N.CC(C)(C)CC[NH2:6].[O:9]=[C:10]1[C:18]2([C:22]3=[CH:23][C:24]4[O:28][CH2:27][O:26][C:25]=4[CH:29]=[C:21]3[O:20][CH2:19]2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]1[CH2:30][C:31]1[O:35][C:34]([C:36]([F:39])([F:38])[F:37])=[C:33]([C:40](O)=[O:41])[CH:32]=1.O=C1C2(COC3C=C4C(=CC2=3)CCO4)C2C(=CC=CC=2)N1CC(O)=O>CO>[O:9]=[C:10]1[C:18]2([C:22]3=[CH:23][C:24]4[O:28][CH2:27][O:26][C:25]=4[CH:29]=[C:21]3[O:20][CH2:19]2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]1[CH2:30][C:31]1[O:35][C:34]([C:36]([F:38])([F:39])[F:37])=[C:33]([C:40]([NH2:6])=[O:41])[CH:32]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 197093,3-DimethylbutylamineHCID 59263485(2'-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,3-indol]-1'(2'H)-yl)acetic acidHCID 685965505-((2'-oxo-6H-spiro[benzofuro[6,5-d][1,3]dioxole-7,3'-indoline]-1'-yl)methyl)-2-(trifluoromethyl)furan-3-carboxylic acid

Product 1

HCID 593523495-[(2'-oxospiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-1'(2'H)-yl)methyl]-2-(trifluoromethyl)furan-3-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following the procedure as described in EXAMPLE 12.49 and making non-critical variations using 7 N ammonia solution in methanol to replace 3,3-dimethylbutylamine, and 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, 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 (86%) as a colorless solid: mp 172-174° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.32-7.27 (m, 1H), 7.20-7.17 (m, 1H), 7.11-7.06 (m, 1H), 6.97-6.94 (m, 1H), 6.70 (s, 1H), 6.49 (s, 1H), 6.09-6.02 (m, 3H), 5.83 (ABq, 2H), 5.85-5.84 (m, 2H), 5.03-4.85 (m, 3H), 4.67-4.64 (m, 1H); MS (ES+) m/z 473.2 (M+1).

Sources & evidence

ORD record
ord-395c704ad6eb48a991c5e27515700628
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

Loading…