2-(Bromomethyl)-5-(trifluoromethyl)furan → 1'-[(5-chloro-1-methyl-1H-imidazol-2-yl)methyl]-2-methylspiro[furo[2,3-f][1,3]benzothiazole-7,3'-indol]-2'(1'H)-one

HRID 1965640Notes

Reaction equation

HRID 1965640 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]2([C:14]3=[CH:15][C:16]4[S:20][CH:19]=[N:18][C:17]=4[CH:21]=[C:13]3[O:12][CH2:11]2)[C:3]1=[O:22].[CH3:23]C1C2C=C3C4(C5C(=CC=CC=5)NC4=O)COC3=CC=2ON=1.Cl.[Cl:46][C:47]1[N:51]([CH3:52])[C:50](CCl)=[N:49][CH:48]=1.BrCC1OC(C(F)(F)F)=CC=1>>[Cl:46][C:47]1[N:51]([CH3:52])[C:50]([CH2:1][N:2]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]3([C:14]4=[CH:15][C:16]5[S:20][C:19]([CH3:23])=[N:18][C:17]=5[CH:21]=[C:13]4[O:12][CH2:11]3)[C:3]2=[O:22])=[N:49][CH:48]=1

Participants

5

Reactant 4

HCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furanHCID 123115195-chloro-2-(chloromethyl)-1-methyl-1H-imidazole hydrochlorideHCID 593524533-methylspiro[furo[3,2-f][1,2]benzisoxazole-5,3'-indol]-2'(1H)-oneHCID 68598575methylspiro[furo[2,3-f][1,3]benzothiazole-7,3'-indol]-2'(1'H)-one

Product 1

HCID 593524181'-[(5-chloro-1-methyl-1H-imidazol-2-yl)methyl]-2-methylspiro[furo[2,3-f][1,3]benzothiazole-7,3'-indol]-2'(1'H)-one

Procedure

Following the procedure as described in EXAMPLE 9 and making non-critical variations using methylspiro[furo[2,3-f][1,3]benzothiazole-7,3′-indol]-2′(1′H)-one to replace 3-methylspiro[furo[3,2-f][1,2]benzisoxazole-5,3′-indol]-2′(1H)-one, and 5-chloro-2-(chloromethyl)-1-methyl-1H-imidazole hydrochloride to replace 2-(bromomethyl)-5-(trifluoromethyl)furan, 1′-[(5-chloro-1-methyl-1H-imidazol-2-yl)methyl]-2-methylspiro[furo[2,3-f][1,3]benzothiazole-7,3′-indol]-2′(1′H)-one was obtained (68%) as a colorless solid: mp 177-178° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ7.63 (dd, J=8.6, 1.1 Hz, 1H), 7.47 (d, J=7.9 Hz, 1H), 7.29-7.23 (m, 1H), 7.08-6.92 (m, 4H), 5.42 (d, J=15.4 Hz, 1H), 5.08-5.00 (m, 1H), 4.85-4.74 (m, 2H), 3.67 (s, 3H), 2.51 (s, 3H); 13C NMR (75 MHz, CDCl3) δ176.8, 169.6, 160.5, 149.1, 142.1, 141.8, 132.1, 129.1, 124.6, 123.7, 123.3, 122.5, 119.6, 119.3, 110.7, 108.7, 81.3, 60.5, 58.2, 38.4, 31.2, 20.2; MS (ES+) m/z 437.0 (M+1), 439.0 (M+1).

Sources & evidence

ORD record
ord-3bbd655a4db941cd97e8286ea17f9dd9
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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