2-Methyl-1,3-benzoxazol-6-amine → N-(6-hydroxy-2,3-dioxo-2,3-dihydro-1H-indol-4-yl)acetamide

HRID 840890Notes

Reaction equation

HRID 840890 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([CH3:9])[O:8][C:4]=2[CH:3]=1.[OH:12][C:13]1[CH:21]=[C:20]2[C:16]([C:17](=[O:23])[C:18](=[O:22])[NH:19]2)=[C:15]([NH:24][C:25](=[O:27])[CH3:26])[CH:14]=1.[CH:28]1[C:33]([NH:34][NH2:35])=[CH:32][CH:31]=[C:30]([S:36]([NH2:39])(=[O:38])=[O:37])[CH:29]=1.Cl>>[OH:12][C:13]1[CH:21]=[C:20]2[C:16]([C:17](=[O:23])[C:18](=[O:22])[NH:19]2)=[C:15]([NH:24][C:25](=[O:27])[CH3:26])[CH:14]=1.[CH3:9][C:7]1[O:8][C:4]2[C:5](=[CH:10][C:11]3[C:14](=[N:35][NH:34][C:33]4[CH:28]=[CH:29][C:30]([S:36]([NH2:39])(=[O:37])=[O:38])=[CH:31][CH:32]=4)[C:13](=[O:12])[NH:1][C:2]=3[CH:3]=2)[N:6]=1

Participants

5

Reactant 3

HCID 5905392-Methyl-1,3-benzoxazol-6-amineHCID 27945674-Hydrazinylbenzenesulfonamide hydrochlorideHCID 21956268N-(6-hydroxy-2,3-dioxo-2,3-dihydro-1H-indol-4-yl)acetamide

Product 2

HCID 21956268N-(6-hydroxy-2,3-dioxo-2,3-dihydro-1H-indol-4-yl)acetamideHCID 1784320444-[2-(2-methyl-6-oxopyrrolo[3,2-f][1,3]benzoxazol-7-yl)hydrazinyl]benzenesulfonamide

Procedure

N-(6-Hydroxy-2,3-dioxo-2,3-dihydro-1H-indol-4-yl)acetamide was prepared from 6-amino-2-methylbenzoxazole (Heleyova, et al., Collection of Czechoslovakian Chemical Communications 1996, 61, 371-80) according to Procedure A in 12% overall yield. Condensation of N-(6-hydroxy-2,3-dioxo-2,3-dihydro-1H-indol-4-yl)acetamide and 4-sulfonamidophenylhydrazine hydrochloride according to Procedure G gave the title compound in 6% yield: 1H NMR (DMSO-d6): δ2.55 (s, 3H), 7.13 (s,1H), 7.23 (s, 2H), 7.57 (d, J=8.8 Hz, 2H), 7.76 (d, J=8.8 Hz, 2H), 7.78 (s, 1H), 11.12 (s, 1H), 12.67 (s, 1H); APCI−MS m/z 370 (M−H)−. Anal. Calcd for C16H15N5O4S: C, 51.75, H, 3.53; N, 18.86; S, 8.86. Found C, 51.50, H, 3.61; N, 18.69; S, 8.49.

Sources & evidence

ORD record
ord-df03dca4064546f2b7f4b1322e6cccd7
Source dataset
uspto-grants-2002_04
Patent number
US06369086B1

Reaction notes

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