HCID 18405518, compound → HCID 57231403, compound

HRID 1018369Notes

Reaction equation

HRID 1018369 reaction equation
C[O:2][C:3](=[O:14])[CH:4]=[CH:5][C:6]1[CH:11]=[C:10]([NH2:12])[CH:9]=[CH:8][C:7]=1[Cl:13].[C:15]12([CH2:25][CH2:26][C:27]3[NH:31][C:30]([CH:32]4[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]4)=[N:29][C:28]=3[C:38](O)=[O:39])[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]3)[CH2:16]1)[CH2:22]2>>[C:15]12([CH2:25][CH2:26][C:27]3[NH:31][C:30]([CH:32]4[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]4)=[N:29][C:28]=3[C:38]([NH:12][C:10]3[CH:9]=[CH:8][C:7]([Cl:13])=[C:6]([CH:5]=[CH:4][C:3]([OH:2])=[O:14])[CH:11]=3)=[O:39])[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]3)[CH2:16]1)[CH2:22]2

Participants

3

Reactant 2

HCID 18405518HCID 18405518, compoundHCID 57089458HCID 57089458, compound

Product 1

HCID 57231403HCID 57231403, compound

Procedure

3-(5-Amino-2-chloro-phenyl)-acrylic acid methyl ester (prepared in two steps from 2-chloro-5-nitro-benzaldehyde) was reacted with 5-(2-adamantan-1-yl-ethyl)-2-cyclohexyl-1H-imidazole-4-carboxylic acid (Example 252) according to the procedure of Example 20, step d. The methyl ester was hydrolysed using the same procedure as in Example 36, step d to afford the title compound. 1H NMR (300 MHz, d6-DMSO) 10.80 (1H, br s), 8.25 (1H, d), 7.96 (1H, d), 7.87 (1H, d), 7.55 (1H, d), 6.44 (1H, d), 2.94 (3H, m), 1.98-1.33 (27H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 55.45; H, 7.91; N, 6.97%. C38H55ClN4O8.5.0 mols H2O requires: C, 55.57; H, 7.98; N, 6.82%.

Sources & evidence

ORD record
ord-d02df034bb9b4b4ebcc1a842e9238416
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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