Trifluoroacetic acid → (E)-3-(1,2,3,4,5,6-hexahydropyrido[2,3-b][1,5]diazocin-8-yl)-N-methyl-N-((3-methylbenzofuran-2-yl)methyl)acrylamide

HRID 1880017ノート

反応式

HRID 1880017 の反応式
[CH3:1][N:2]([CH2:26][C:27]1[O:28][C:29]2[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=2[C:31]=1[CH3:32])[C:3](=[O:25])/[CH:4]=[CH:5]/[C:6]1[CH:24]=[N:23][C:9]2[NH:10][CH2:11][CH2:12][CH2:13][N:14](C(OC(C)(C)C)=O)[CH2:15][C:8]=2[CH:7]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH:10]1[CH2:11][CH2:12][CH2:13][NH:14][CH2:15][C:8]2[CH:7]=[C:6](/[CH:5]=[CH:4]/[C:3]([N:2]([CH3:1])[CH2:26][C:27]3[O:28][C:29]4[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=4[C:31]=3[CH3:32])=[O:25])[CH:24]=[N:23][C:9]1=2

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 68412763(E)-tert-butyl 8-(3-(methyl((3-methylbenzofuran-2-yl)methyl)amino)-3-oxoprop-1-enyl)-1,2,3,4-tetrahydropyrido[2,3-b][1,5]diazocine-5(6H)-carboxylate

生成物 1

HCID 24891659(E)-3-(1,2,3,4,5,6-hexahydropyrido[2,3-b][1,5]diazocin-8-yl)-N-methyl-N-((3-methylbenzofuran-2-yl)methyl)acrylamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(E)-tert-butyl 8-(3-(methyl((3-methylbenzofuran-2-yl)methyl)amino)-3-oxoprop-1-enyl)-1,2,3,4-tetrahydropyrido[2,3-b][1,5]diazocine-5(6H)-carboxylate (49 mg, 0.1 mmol) was dissolved in 5 mL of DCM followed by the addition of trifluoroacetic acid (5 mL). The solution was stirred for 1.5 h, then concentrated in vacuo, and subjected to prep HPLC purification to obtain the product as a white solid. Yield 25 mg (64%); 1H NMR (400 MHz, CDCl3) δ 10.1 (bs, 1H), 8.01 (m, 2H), 7.50-7.22 (m, 6H), 6.86 (d, J=16.0 Hz, 1H), 4.79 (s, 2H), 4.66 (s, 2H), 3.88 (s, 2H), 3.25 (s, 2H), 3.10 (s, 3H), 2.29 (bs, 5H); ESI MS m/z 391 [C23H26N4O2+H]+

後処理

  1. concentrationconcentrated in vacuo
  2. customHPLC purification

出典と根拠

ORDレコード
ord-cbc1431d3b6a40a99455a378d0e8cc24
出典データセット
uspto-grants-2012_11
特許番号
US08318720B2

反応ノート

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