2,4-Dioxo-5-thiazolidineacetic acid → 6-{4-[2-(2,4-Dioxo-thiazolidin-5-yl)-acetyl]-piperazin-1-yl}-N-(3-iodo-4-methyl-phenyl)-nicotinamide

HRID 2190656Notes

Reaction equation

HRID 2190656 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:23])[C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[N:13][CH:12]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[O:24]=[C:25]1[NH:29][C:28](=[O:30])[CH:27]([CH2:31][C:32](O)=[O:33])[S:26]1.COC(C1CCC(C(N2CCN(C3C=CC(C(=O)NC4C=CC=C(C(C)(C)C)C=4)=CN=3)CC2)=O)CC1)=O>>[O:24]=[C:25]1[NH:29][C:28](=[O:30])[CH:27]([CH2:31][C:32]([N:20]2[CH2:19][CH2:18][N:17]([C:14]3[CH:15]=[CH:16][C:11]([C:10]([NH:9][C:4]4[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([I:1])[CH:3]=4)=[O:23])=[CH:12][N:13]=3)[CH2:22][CH2:21]2)=[O:33])[S:26]1

Participants

4

Reactant 3

HCID 6450302,4-Dioxo-5-thiazolidineacetic acidHCID 59318071N-(3-Iodo-4-methyl-phenyl)-6-piperazin-1-yl-nicotinamideHCID 593180854-{4-[5-(3-tert-Butyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carbonyl}-cyclohexanecarboxylic acid methyl ester

Product 1

HCID 593181436-{4-[2-(2,4-Dioxo-thiazolidin-5-yl)-acetyl]-piperazin-1-yl}-N-(3-iodo-4-methyl-phenyl)-nicotinamide

Procedure

6-{4-[2-(2,4-Dioxo-thiazolidin-5-yl)-acetyl]-piperazin-1-yl}-N-(3-iodo-4-methyl-phenyl)-nicotinamide was synthesized by the ECDI coupling of N-(3-iodo-4-methyl-phenyl)-6-piperazin-1-yl-nicotinamide and 2-(2,4-dioxo-thiazolidin-5-yl)-acetic acid in a manner similar to the one described in the synthesis of 4-{4-[5-(3-tert-butyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carbonyl}-cyclohexanecarboxylic acid methyl ester, above. LCMS calcd for C22H22IN5O4S (m/e) 579, obsd 580 (M+H).

Sources & evidence

ORD record
ord-9aac2efc200b4418925e511dba85aa52
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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