3-(hydroxymethyl)-3-(5-hydroxy-2-methyl-1,3-benzothiazol-6-yl)-1-pentyl-1,3-dihydro-2H-indol-2-one → 2-methyl-1'-pentylspiro[furo[2,3-f][1,3]benzothiazole-7,3'-indol]-2'(1'H)-one

HRID 425618Notes

Reaction equation

HRID 425618 reaction equation
O[CH2:2][C:3]1([C:18]2[C:27]([OH:28])=[CH:26][C:21]3[N:22]=[C:23]([CH3:25])[S:24][C:20]=3[CH:19]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:4]1=[O:17].ClC1C=CC(Cl)=C2C=1C(C1C(O)=CC3OCOC=3C=1)(CO)C(=O)N2CCCCC>>[CH3:25][C:23]1[S:24][C:20]2[CH:19]=[C:18]3[C:3]4([CH2:2][O:28][C:27]3=[CH:26][C:21]=2[N:22]=1)[C:11]1[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=1)[N:5]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:4]4=[O:17]

Participants

3

Reactant 2

HCID 588724613-(hydroxymethyl)-3-(5-hydroxy-2-methyl-1,3-benzothiazol-6-yl)-1-pentyl-1,3-dihydro-2H-indol-2-oneHCID 588724744,7-dichloro-3-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-1-pentyl-1,3-dihydro-2H-indol-2-one

Product 1

HCID 592634762-methyl-1'-pentylspiro[furo[2,3-f][1,3]benzothiazole-7,3'-indol]-2'(1'H)-one

Procedure

Following the procedure as described in EXAMPLE 1.22, and making non-critical variations using 3-(hydroxymethyl)-3-(5-hydroxy-2-methyl-1,3-benzothiazol-6-yl)-1-pentyl-1,3-dihydro-2H-indol-2-one to replace 4,7-dichloro-3-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-1-pentyl-1,3-dihydro-2H-indol-2-one, the title compound was obtained (50%) as a white solid: mp 105-107° C.; 1H NMR (300 MHz, CDCl3) δ 7.59 (d, 1H), 7.28 (dt, 1H), 7.02-6.92 (m, 2H), 5.02 (d, 1H), 4.77 (d, 1H), 4.01 (m, 1H), 3.64 (m, 1H), 2.54 (s, 3H), 1.92-1.71 (m, 2H), 1.54-1.34 (m, 4H), 0.92 (t, 3H); 13C NMR (75 MHz, CDCl3) δ 176.7, 169.2, 160.2, 149.2, 142.7, 138.3, 132.7, 129.0, 128.6, 123.5, 122.7, 122.1, 120.2, 108.6, 108.3, 80.1, 58.1, 40.7, 29.1, 27.0, 22.5, 20.2, 14.1; MS (ES+) m/z 379.5 (M+1).

Sources & evidence

ORD record
ord-3c4e5597e96a4a9794e08f7187a16ad7
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

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