N-Methyl-D-glucamine → 3-{[2-(2-Adamantan-1-yl-ethyl)-5-o-tolyl-1H-pyrrole-3-carbonyl]-amino}-benzoic Acid

HRID 1018332ノート

反応式

HRID 1018332 の反応式
C([O:3][C:4](=O)[CH2:5][C:6](=O)[CH2:7][CH2:8][C:9]12[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2)C.[CH3:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28](=O)[CH2:29]Br.C([O:39][C:40](=[O:48])[C:41]1[CH:46]=[CH:45][CH:44]=[C:43]([NH2:47])[CH:42]=1)C1C=CC=CC=1.C(OC(=O)C1C=C([NH2:74])C=C(C(OCC2C=CC=CC=2)=O)C=1)C1C=CC=CC=1.CNC[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O>O.O.O1CCOCC1>[C:9]12([CH2:8][CH2:7][C:6]3[NH:74][C:28]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[CH3:21])=[CH:29][C:5]=3[C:4]([NH:47][C:43]3[CH:42]=[C:41]([CH:46]=[CH:45][CH:44]=3)[C:40]([OH:39])=[O:48])=[O:3])[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2

参加物

8

反応物 5

HCID 8567N-Methyl-D-glucamineHCID 7023592Dibenzyl 5-aminoisophthalateHCID 124306762-Bromo-2'-methylacetophenoneHCID 15428374Benzyl 3-aminobenzoateHCID 538974675-Adamantan-1-yl-3-oxo-pentanoic acid ethyl ester

生成物 1

HCID 116647283-{[2-(2-Adamantan-1-yl-ethyl)-5-o-tolyl-1H-pyrrole-3-carbonyl]-amino}-benzoic Acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 218864351,4-Dioxane--water (1/1)溶媒

実験手順

The title compound was synthesised following the procedure of Example 1, with the modification that 5-adamantan-1-yl-3-oxo-pentanoic acid ethyl ester was used instead of 4-adamantan-1-yl-3-oxo-butyric acid ethyl ester, and o-methyl-2-bromo-1-phenyl-ethanone was used instead of 2-bromo-1-phenyl-ethanone in step a, and 3-amino-benzoic acid benzyl ester replaced 5-amino-isophthalic acid dibenzyl ester in step d. 1H NMR (300 MHz, d6-DMSO) 13.0 (1H, br s), 11.22 (1H, s), 9.51 (1H, s), 8.32 (1H, s), 8.02 (1H, d), 7.60 (1H, d), 7.40 (2H, m), 7.25 (3H, m), 6.88 (1H, s), 2.95 (2H, m), 2.45 (3H, s), 1.94 (3H, s), 1.64 (6H, m), 1.53 (6H, s), 1.36 (2H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 64.72; H, 7.77; N, 5.87%. C38H51N3O8.1.5 H2O requires: C, 64.72; H, 7.72, N, 5.96%.

出典と根拠

ORDレコード
ord-3ef322da784a4e4b8e2ea680e7a08a1e
出典データセット
uspto-grants-2002_11
特許番号
US06479531B1

反応ノート

読み込み中…