1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178440932, compound

HRID 2190658Notes

Reaction equation

HRID 2190658 reaction equation
CCN=C=NCCCN(C)C.[C:12]([C:16]1[CH:17]=[C:18]([NH:22][C:23](=[O:36])[C:24]2[CH:29]=[CH:28][C:27]([N:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)=[N:26][CH:25]=2)[CH:19]=[CH:20][CH:21]=1)([CH3:15])([CH3:14])[CH3:13].[OH:37][C:38]1[CH:42]=[C:41]([CH2:43][CH2:44][C:45](O)=[O:46])[O:40][N:39]=1.COC(C1CCC(C(N2CCN(C3C=CC(C(=O)NC4C=CC=C(C(C)(C)C)C=4)=CN=3)CC2)=O)CC1)=O>>[C:12]([C:16]1[CH:17]=[C:18]([NH:22][C:23](=[O:36])[C:24]2[CH:29]=[CH:28][C:27]([N:30]3[CH2:35][CH2:34][N:33]([C:45](=[O:46])[CH2:44][CH2:43][C:41]4[O:40][N:39]=[C:38]([OH:37])[CH:42]=4)[CH2:32][CH2:31]3)=[N:26][CH:25]=2)[CH:19]=[CH:20][CH:21]=1)([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 593180854-{4-[5-(3-tert-Butyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carbonyl}-cyclohexanecarboxylic acid methyl esterHCID 59318114N-(3-tert-Butyl-phenyl)-6-piperazin-1-yl-nicotinamideHCID 1785253353-(3-Hydroxy-5-isoxazolyl)propanoic acid

Product 1

HCID 178440932HCID 178440932, compound

Procedure

N-(3-tert-Butyl-phenyl)-6-{4-[3-(3-hydroxy-isoxazol-5-yl)-propionyl]-piperazin-1-yl}-nicotinamide was synthesized from the EDCI coupling of N-(3-tert-butyl-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 C26H31N5O4 (m/e) 477, obsd 478 (M+H).

Sources & evidence

ORD record
ord-b92241e19dc147c38a25dc6abb4f866c
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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