8-hydroxy-8-(7-hydroxy-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-6-isopentyl-6H-thiazolo[5,4-e]indol-7(8H)-one → 8-(7-hydroxy-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-6-isopentyl-6H-thiazolo[5,4-e]indol-7(8H)-one

HRID 1965274Notes

Reaction equation

HRID 1965274 reaction equation
O[C:2]1([C:20]2[C:29]([OH:30])=[CH:28][C:23]3[O:24][CH2:25][CH2:26][O:27][C:22]=3[CH:21]=2)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]3[N:13]=[CH:12][S:11][C:9]3=2)[N:4]([CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[C:3]1=[O:19].C1(C(C2C=CC=CC=2)N2C3C(=CC=CC=3)C(O)(C3C=CC(OC)=CC=3O)C2=O)C=CC=CC=1>>[OH:30][C:29]1[C:20]([CH:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]4[N:13]=[CH:12][S:11][C:9]4=3)[N:4]([CH2:14][CH2:15][CH:16]([CH3:17])[CH3:18])[C:3]2=[O:19])=[CH:21][C:22]2[O:27][CH2:26][CH2:25][O:24][C:23]=2[CH:28]=1

Participants

3

Reactant 2

HCID 673561578-hydroxy-8-(7-hydroxy-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-6-isopentyl-6H-thiazolo[5,4-e]indol-7(8H)-oneHCID 673568351-(diphenylmethyl)-3-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 686001138-(7-hydroxy-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-6-isopentyl-6H-thiazolo[5,4-e]indol-7(8H)-one

Procedure

Following the procedure as described in PREPARATION 12B, and making non-critical variations using 8-hydroxy-8-(7-hydroxy-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-6-isopentyl-6H-thiazolo[5,4-e]indol-7(8H)-one to replace 1-(diphenylmethyl)-3-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-1,3-dihydro-2H-indol-2-one, 8-(7-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-6-(3-methylbutyl)-6,8-dihydro-7H-[1,3]thiazolo[5,4-e]indol-7-one was obtained (93%): MS (ES+) m/z 411.0 (M+1).

Sources & evidence

ORD record
ord-170b8c9551b84b47b44b8ca660eda9f6
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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