HCID 15389740, compound → HCID 178488077, compound

HRID 1244478Notes

Reaction equation

Cl.CC(C1C=[C:8](C=C(C(C)(C)C)C=1O)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)=[NH:20])=[CH:14][CH:13]=1)=O)(C)C.[CH3:34][O:35][C:36]1[CH:37]=[C:38]2[C:42](=[CH:43][CH:44]=1)[NH:41][CH:40]=[C:39]2[CH2:45][C:46]([N:48]1CCN(C2C=CC(N)=CC=2)[CH2:50][CH2:49]1)=[O:47].CC(C1C=C(C=C(C(C)(C)C)C=1O)C(NC1C=CC(N)=CC=1)=O)(C)C>>[CH3:34][O:35][C:36]1[CH:37]=[C:38]2[C:42](=[CH:43][CH:44]=1)[NH:41][CH:40]=[C:39]2[CH2:45][C:46]([N:48]1[CH2:8][CH2:9][N:11]([C:12]2[CH:13]=[CH:14][C:15]([NH:18][C:19]([C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)=[NH:20])=[CH:16][CH:17]=2)[CH2:50][CH2:49]1)=[O:47]

Participants

Reactant 3

HCID 15389740HCID 15389740, compound

HCID 22987726HCID 22987726, compound

HCID 178441077HCID 178441077, compound

Product 1

HCID 178488077HCID 178488077, compoundYield 20%

Procedure

The experimental protocol used is the same as that described for the compound 1, with 1-[(5 methoxy-1H-indole-3-yl)methylcarbonyl]-4-(4-aminophenyl)-piperazine replacing the 3,5-bis-(1,1-dimethylethyl)-4-hydroxy-N-(4-aminophenyl)-benzamide. The expected product is isolated in the form of the free base with a yield of 20% (pale yellow powder). Melting point: 221-222° C. NMR 1H (400 MHz, DMSO d6, δ): 10.78 (s, 1 H, indolic NH); 7.72 (m, 1 H, thiophene); 7.59 (m, 1 H, thiophene); 7.22 (d, 1 H, indole, J=8.7 Hz); 7.19 (m, 1 H, thiophene); 7.09 (m, 2 H, indole); 6.82 (m, 4 H, Ph); 6.72 (m, 1 H indole); 6.35 (s, 2 H, NH2); 3.80 (s, 2 H, CH2); 3.73 (s, 3 H, CH3); 3.62 (m, 4 H, piperazine); 2.95 (m, 4 H, piperazine).

Sources & evidence

ORD record: ord-4c1d6e167eca448183f91e5eb6454929
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07122535B2

Reaction notes

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