2,4-Dioxo-5-thiazolidineacetic acid → 4,5-Dichloro-1-ethyl-1H-indole-2-carboxylic acid (4-{4-[2-(2,4-dioxo-thiazolidin-5-yl)-acetyl]-piperazin-1-yl}-phenyl)-amide

HRID 1645359Notes

Reaction equation

HRID 1645359 reaction equation
Cl.[O:2]=[C:3]1[NH:7][C:6](=[O:8])[CH:5]([CH2:9][C:10](N2CCN(C3C=CC(NC(C4N(CC)C5C(C=4)=C(OCC)C=CC=5)=O)=CC=3)CC2)=[O:11])[S:4]1.[N:41]1([C:47]2[CH:52]=[CH:51][C:50]([NH:53][C:54]([C:56]3[N:57]([CH2:67][CH3:68])[C:58]4[C:63]([CH:64]=3)=[C:62]([Cl:65])[C:61]([Cl:66])=[CH:60][CH:59]=4)=[O:55])=[CH:49][CH:48]=2)[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1.O=C1NC(=O)C(CC(O)=O)S1>>[O:2]=[C:3]1[NH:7][C:6](=[O:8])[CH:5]([CH2:9][C:10]([N:44]2[CH2:45][CH2:46][N:41]([C:47]3[CH:52]=[CH:51][C:50]([NH:53][C:54]([C:56]4[N:57]([CH2:67][CH3:68])[C:58]5[C:63]([CH:64]=4)=[C:62]([Cl:65])[C:61]([Cl:66])=[CH:60][CH:59]=5)=[O:55])=[CH:49][CH:48]=3)[CH2:42][CH2:43]2)=[O:11])[S:4]1

Participants

4

Reactant 3

HCID 6450302,4-Dioxo-5-thiazolidineacetic acidHCID 593651424,5-dichloro-1-ethyl-1H-indole-2-carboxylic acid (4-piperazin-1-yl-phenyl)-amideHCID 866424164-ethoxy-1-ethyl-1H-indole-2-carboxylic acid (4-{4-[2-(2,4-dioxo-thiazolidin-5-yl)-acetyl]-piperazin-1-yl}-phenyl)-amide hydrochloride

Product 1

HCID 593651994,5-Dichloro-1-ethyl-1H-indole-2-carboxylic acid (4-{4-[2-(2,4-dioxo-thiazolidin-5-yl)-acetyl]-piperazin-1-yl}-phenyl)-amide

Procedure

With a method similar to that used for the preparation of 4-ethoxy-1-ethyl-1H-indole-2-carboxylic acid (4-{4-[2-(2,4-dioxo-thiazolidin-5-yl)-acetyl]-piperazin-1-yl}-phenyl)-amide hydrochloride, 4,5-dichloro-1-ethyl-1,1-indole-2-carboxylic acid (4-{4-[2-(2,4-dioxo-thiazolidin-5-yl)-acetyl]-piperazin-1-yl}-phenyl)-amide was prepared from 4,5-dichloro-1-ethyl-1H-indole-2-carboxylic acid (4-piperazin-1-yl-phenyl)-amide and (2,4-dioxo-thiazolidin-5-yl)-acetic acid. LCMS for C26H25Cl2N5O4S calcd. (m/e) 573, observed 574 (M+H).

Sources & evidence

ORD record
ord-7e3640f4b0234edb9fea23ea0f4a77af
Source dataset
uspto-grants-2012_02
Patent number
US08124766B2

Reaction notes

Loading…