Triethylamine → [2-(4-{4-[N'-(3,5-Diamino-6-chloropyrazine-2-carbonyl)guanidino]butyl}phenoxy)ethyl]-carbamic acid tert-butyl ester

HRID 81322ノート

反応式

HRID 81322 の反応式
[C:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][NH2:21])=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].I.[NH2:24][C:25]1[C:26]([C:33]([NH:35][C:36](=[NH:39])SC)=[O:34])=[N:27][C:28]([Cl:32])=[C:29]([NH2:31])[N:30]=1.C(N(CC)CC)C>C1COCC1>[C:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:36]([NH2:39])=[N:35][C:33]([C:26]2[C:25]([NH2:24])=[N:30][C:29]([NH2:31])=[C:28]([Cl:32])[N:27]=2)=[O:34])=[CH:13][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 22566154{2-[4-(4-Aminobutyl)phenoxy]ethyl}carbamic acid tert-butyl esterHCID 140329753methyl N-(3,5-diamino-6-chloropyrazine-2-carbonyl)carbamimidothioate;hydroiodide

生成物 1

HCID 178453722[2-(4-{4-[N'-(3,5-Diamino-6-chloropyrazine-2-carbonyl)guanidino]butyl}phenoxy)ethyl]-carbamic acid tert-butyl ester収率 92.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

{2-[4-(4-Aminobutyl)phenoxy]ethyl}carbamic acid tert-butyl ester 2 (1.7 g, 5.5 mmol), 1-(3,5-diamino-6-chloropyrazine-2-carbonyl)-2-methylisothiourea hydriodide (2.6 g, 6.6 mmol), and triethylamine (3.1 mL) were combined in THF (18 mL). The reaction was stirred at reflux under argon for 1.5 h. The product mixture was allowed to cool, and the solvent was evaporated. Chromatography (silica gel, methylene chloride/methanol/concentrated ammonium hydroxide, 100:10:1) afforded 2.65 g (92%) of the pure product as a yellow foamy solid. 1H NMR (300 MHz, CDCl3) δ 1.44 (s, 9H), 1.62 (m, 2H), 1.61 (m, 2H), 1.75 (br s, 2H), 2.56 (t, 2H), 2.71 (t, 2H), 3.51 (m, 2H), 3.99 (t, 2H), 5.07 (br s, 1H), 6.80 (d, 2H), 7.08 (d, 2H).

後処理

  1. temperatureat reflux under argon for 1.5 h
  2. temperatureto cool
  3. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-b3ba4fdb56fd4d26a0f489f6e331e680
出典データセット
uspto-grants-2014_09
特許番号
US08846688B2

反応ノート

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