HCID 66965643、化合物 → 2-[2,6-dimethyl-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-3H-benzoimidazole-5-carboxylic acid (3,4-dimethyl-phenyl)-amide

HRID 1514883ノート

反応式

HRID 1514883 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[NH2:19])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([CH3:15])[CH:9]=1)=[O:6].[CH3:20][C:21]1[CH:28]=[C:27]([O:29][CH2:30][CH2:31][N:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)[CH:26]=[C:25]([CH3:37])[C:22]=1[CH:23]=O>CO>[CH3:15][C:10]1[CH:9]=[C:8]([NH:7][C:5]([C:4]2[CH:16]=[CH:17][C:18]3[N:19]=[C:23]([C:22]4[C:21]([CH3:20])=[CH:28][C:27]([O:29][CH2:30][CH2:31][N:32]5[CH2:36][CH2:35][CH2:34][CH2:33]5)=[CH:26][C:25]=4[CH3:37])[NH:1][C:2]=3[CH:3]=2)=[O:6])[CH:13]=[CH:12][C:11]=1[CH3:14]

参加物

4

反応物 2

HCID 66965643HCID 66965643、化合物HCID 866512592,6-Dimethyl-4-(2-pyrrolidin-1-yl-ethoxy)-benzaldehyde

生成物 1

HCID 669658422-[2,6-dimethyl-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-3H-benzoimidazole-5-carboxylic acid (3,4-dimethyl-phenyl)-amide

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of 3,4-diamino-N-(3,4-dimethyl-phenyl)-benzamide (0.1 mL in 0.2 M DMSO solution), 2,6-dimethyl-4-(2-pyrrolidin-1-yl-ethoxy)-benzaldehyde (0.1 mL in 0.2 M toluene solution) and FeCl3 (0.05 mL in 0.02M THF solution) was stirred in open air at ambient temperature overnight. The mixture was then diluted by MeOH and the whole was loaded onto a solid phase extraction (SPE) cartridge that contained strong cation exchange (SCX) (1 g media in 6 mL cartridge, United Chemical Technology). Wash-to-waste (5 mL MeOH) was followed by elute-to-collect (5 mL 20:2:1 ethyl acetate-MeOH-Et3N) and, after evaporation of volatiles, the crude was further purified by silica gel column chromatography to give 2-[2,6-dimethyl-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-3H-benzoimidazole-5-carboxylic acid (3,4-dimethyl-phenyl)-amide: MS (m/z) 483 (M+1).

後処理

  1. extractionthe whole was loaded onto a solid phase extraction (SPE) cartridge that
  2. washWash-to-waste (5 mL MeOH)
  3. customby elute-to-collect (5 mL 20:2:1 ethyl acetate-MeOH-Et3N)
  4. customafter evaporation of volatiles
  5. customthe crude was further purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-b42d5cf064b4448db55a00fd183600a3
出典データセット
uspto-grants-2012_07
特許番号
US08222248B2

反応ノート

読み込み中…