1-(5-amino-2,3-dihydro-1H-indol-1-yl)ethan-1-one → HCID 21956269, compound
Reaction equation
C(N1C2C(=CC(N)=CC=2)CC1)(=O)C.[C:14]([N:17]1[C:25]2[CH:24]=[C:23]3[C:26](=[O:30])[C:27](=[O:29])[NH:28][C:22]3=[CH:21][C:20]=2[CH2:19][CH2:18]1)(=[O:16])[CH3:15].[CH:31]1[C:36]([NH:37][NH2:38])=[CH:35][CH:34]=[C:33]([S:39]([NH2:42])(=[O:41])=[O:40])[CH:32]=1.Cl>>[C:14]([N:17]1[C:25]2[CH:24]=[C:23]3[C:26](=[O:30])[C:27](=[O:29])[NH:28][C:22]3=[CH:21][C:20]=2[CH2:19][CH2:18]1)(=[O:16])[CH3:15].[C:14]([N:17]1[C:25]2[CH:24]=[C:23]3[C:26](=[N:38][NH:37][C:36]4[CH:35]=[CH:34][C:33]([S:39]([NH2:42])(=[O:40])=[O:41])=[CH:32][CH:31]=4)[C:27](=[O:29])[NH:28][C:22]3=[CH:21][C:20]=2[CH2:19][CH2:18]1)(=[O:16])[CH3:15]Participants
Procedure
5-Acetyl-1,5,6,7-tetrahydro-pyrrolo[2,3-f]indole-2,3-dione was prepared from 1-acetyl-5-aminoindoline according to Procedure A in 90% yield: mp>250° C.; 1H NMR (DMSO-d6): δ 2.11 (s, 3H), 3.16 (t, J=8.4 Hz, 2H), 4.06 (t, J=8.4 Hz, 2H), 6.78 (s, 1H), 8.02 (s, 1H), 10.87 (s, 1H); APCI-MS: m/z 229 (M−H)−. Anal. Calcd for C12H10N2O3.0.3H2O: C, 61.17; H, 4.53; N, 11.89. Found: C, 60.91; H, 4.62; N, 12.10. The title compound was prepared from 5-acetyl-1,5,6,7-tetrahydro-pyrrolo[2,3-f]indole-2,3-dione and 4-sulfonamidophenylhydrazine hydrochloride according to Procedure G in 53% yield: mp>250° C.; 1H NMR (DMSO-d6): d2.13 (s, 3H), 3.13 (t, J=8.4 Hz, 2H), 4.06 (t, J=8.4 Hz, 2H), 6.79 (s, 1H), 7.22 (s, 2H), 7.48 (d, J=8.7 Hz, 2H), 7.76 (d, J=8.7 Hz, 2H), 8.24 (s, 1H), 10.96 (s, 1H), 12.78 (s, 1H); APCI-MS: m/z 422 (M+Na)+. Anal. Calcd for C18H17N5O4S: C, 54.13; H, 4.29; N, 17.53; S, 8.03. Found: C, 53.85; H, 4.23; N, 17.28; S, 7.89.
Sources & evidence
- ORD record
- ord-0c53d6380bb44be184e3dc36cb440fbf
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07105529B2
Reaction notes
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