1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 6-{4-[3-(3-Hydroxy-isoxazol-5-yl)-propionyl]-piperazin-1-yl}-N-(3-iodo-4-methyl-phenyl)-nicotinamide

HRID 2190659Notes

Reaction equation

HRID 2190659 reaction equation
CCN=C=NCCCN(C)C.[I:12][C:13]1[CH:14]=[C:15]([NH:20][C:21](=[O:34])[C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[N:24][CH:23]=2)[CH:16]=[CH:17][C:18]=1[CH3:19].[OH:35][C:36]1[CH:40]=[C:39]([CH2:41][CH2:42][C:43](O)=[O:44])[O:38][N:37]=1.COC(C1CCC(C(N2CCN(C3C=CC(C(=O)NC4C=CC=C(C(C)(C)C)C=4)=CN=3)CC2)=O)CC1)=O>>[OH:35][C:36]1[CH:40]=[C:39]([CH2:41][CH2:42][C:43]([N:31]2[CH2:30][CH2:29][N:28]([C:25]3[CH:26]=[CH:27][C:22]([C:21]([NH:20][C:15]4[CH:16]=[CH:17][C:18]([CH3:19])=[C:13]([I:12])[CH:14]=4)=[O:34])=[CH:23][N:24]=3)[CH2:33][CH2:32]2)=[O:44])[O:38][N:37]=1

Participants

5

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 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 esterHCID 1785253353-(3-Hydroxy-5-isoxazolyl)propanoic acid

Product 1

HCID 1784265686-{4-[3-(3-Hydroxy-isoxazol-5-yl)-propionyl]-piperazin-1-yl}-N-(3-iodo-4-methyl-phenyl)-nicotinamide

Procedure

6-{4-[3-(3-Hydroxy-isoxazol-5-yl)-propionyl]-piperazin-1-yl}-N-(3-iodo-4-methyl-phenyl)-nicotinamide was synthesized from the EDCI coupling of N-(3-iodo-4-methyl-phenyl)-6-piperazin-1-yl-nicotinamide and 3-(3-hydroxy-isoxazol-5-yl)-propionic 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 C23H24IN5O4 (m/e) 561, obsd 562 (M+H),

Sources & evidence

ORD record
ord-58d2b7d856484c0297c77f9c2fd5c0fa
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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