Hydrochloric Acid → N-(3-amidinophenyl)-N'-(1-benzylpiperidin-4-yl)cycloheptylurea

HRID 1059529ノート

反応式

HRID 1059529 の反応式
Cl.[C:2]([C:4]1[CH:5]=[C:6]([N:10]([CH:27]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[C:11]([NH:13][CH:14]2[CH2:19][CH2:18][N:17]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:16][CH2:15]2)=[O:12])[CH:7]=[CH:8][CH:9]=1)#[N:3].C(=O)([O-])[O-].[NH4+:38].[NH4+]>C(O)C>[C:2]([C:4]1[CH:5]=[C:6]([N:10]([CH:27]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[C:11]([NH:13][CH:14]2[CH2:19][CH2:18][N:17]([CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:16][CH2:15]2)=[O:12])[CH:7]=[CH:8][CH:9]=1)(=[NH:38])[NH2:3]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 517111Ammonium CarbonateHCID 53879433N-(3-Cyanophenyl)-N'-(1-benzylpiperidin-4-yl)cycloheptylurea

生成物 1

HCID 54137994N-(3-amidinophenyl)-N'-(1-benzylpiperidin-4-yl)cycloheptylurea

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Dry hydrogen chloride gas was bubbled through an ice cooled solution of N-(3-cyanophenyl)-N′-(1-benzylpiperidin-4-yl)cycloheptylurea (0.03 g, 0.077 mmol) in anhydrous ethanol (10 ml) under a nitrogen atmosphere for 15 min. The reaction was stoppered, allowed to warm to ambient temperature and stirred for 24 h. The reaction was concentrated to a solid and dissolved in anhydrous ethanol (5 ml) and ammonium carbonate (0.023 g, 0.23 mmol) was added. The reaction mixture was stirred at ambient temperature overnight then was concentrated in vacuo. N-(3-Amidinophenyl)-N′-(1-benzylpiperidin-4-yl)cycloheptylurea was purified by HPLC on a Vydec® C-18 column eluting with solvent mixture A (acetonitrile:water:TFA 80:20:0.3) and solvent mixture B (water:TFA 99.7:0.3) using a gradient starting with A:B at 3:97 and changing to A:B at 70:30 over 15 min. The major fraction eluting at 15 minutes was concentrated to give N-(3-amidinophenyl)-N′-(1-benzylpiperidin-4-yl)cycloheptylurea as an amorphous solid; LRMS (M+H)+ m/z 406, (M+2H)+2 m/z 203.8; 1H NMR (DMSO-d6): 9.52(broad s, 1H), 9.27(s, 2H), 9.02(s, 2H), 7.5(m, 9H), 4.3(m,m, 2H), 3.95(m, 1H), 3.67(m, 2H), 3.42(m, 2H), 3.2(m,2H), 3.1(m, 2H), 2.05-1.6(m, 8H).

後処理

  1. concentrationThe reaction was concentrated to a solid
  2. dissolutiondissolved in anhydrous ethanol (5 ml)
  3. stirringThe reaction mixture was stirred at ambient temperature overnight
  4. concentrationthen was concentrated in vacuo
  5. customN-(3-Amidinophenyl)-N′-(1-benzylpiperidin-4-yl)cycloheptylurea was purified by HPLC on a Vydec® C-18 column
  6. washeluting with solvent mixture A (acetonitrile:water:TFA 80:20:0.3) and solvent mixture B (water:TFA 99.7:0.3)
  7. customover 15 min
  8. washThe major fraction eluting at 15 minutes
  9. concentrationwas concentrated

出典と根拠

ORDレコード
ord-5b1286f3955d4a3db35d624edf075b00
出典データセット
uspto-grants-2003_02
特許番号
US06521614B1

反応ノート

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