Triethylamine → N-Cyclohexyl-N-(2,2-dimethoxyethyl)-3-(3-(1-ethyl-1H-1,2,3-triazol-4-yl)phenethoxy)propanamide

HRID 909893ノート

反応式

HRID 909893 の反応式
C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.[CH3:19][O:20][CH:21]([O:30][CH3:31])[CH2:22][NH:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.[CH2:32]([N:34]1[CH:38]=[C:37]([C:39]2[CH:40]=[C:41]([CH:50]=[CH:51][CH:52]=2)[CH2:42][CH2:43][O:44][CH2:45][CH2:46][C:47](O)=[O:48])[N:36]=[N:35]1)[CH3:33].C(N(CC)CC)C>C1COCC1.C(#N)C.C(OCC)(=O)C>[CH:24]1([N:23]([CH2:22][CH:21]([O:30][CH3:31])[O:20][CH3:19])[C:47](=[O:48])[CH2:46][CH2:45][O:44][CH2:43][CH2:42][C:41]2[CH:50]=[CH:51][CH:52]=[C:39]([C:37]3[N:36]=[N:35][N:34]([CH2:32][CH3:33])[CH:38]=3)[CH:40]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 3024915N-(2,2-dimethoxyethyl)cyclohexanamineHCID 670761313-(3-(1-Ethyl-1H-1,2,3-triazol-4-yl)phenethoxy)propanoic acid

生成物 1

HCID 67075953N-Cyclohexyl-N-(2,2-dimethoxyethyl)-3-(3-(1-ethyl-1H-1,2,3-triazol-4-yl)phenethoxy)propanamide

試薬・触媒・溶媒 3

HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
25 °C

実験手順

A solution of T3P (1.41 mL) dissolved in THF (1.57M) was added in one portion to a stirred solution of N-(2,2-dimethoxyethyl)cyclohexanamine (0.24 mL), 3-(3-(1-ethyl-1H-1,2,3-triazol-4-yl)phenethoxy)propanoic acid [Example 4, Step iv)] (0.45 g), and triethylamine (1.86 mL) in acetonitrile (5 mL) at 25° C. The resulting solution was stirred at 25° C. for 15 min. The reaction mixture was diluted with ethyl acetate (50 mL), and washed with saturated sodium hydrogen carbonate (20 mL). The organic layer was dried over magnesium sulfate, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0-70% ethyl acetate in isohexane to afford the subtitled compound (0.46 g). 1H NMR (400 MHz, CD3OD) δ 8.32 and 8.31 (2×s, 1H), 7.68 and 7.66 (2×s, 1H), 7.65-7.61 (m, 1H), 7.32 and 7.32 (2×t, J=7.5 Hz, 1H), 7.22-7.18 (m, 1H), 4.52 and 4.36 (2×t, J=5.3 Hz, 1H), 4.47 (q, J=7.3 Hz, 2H), 4.04-3.94 (m, 1H), 3.76-3.61 (m, 4H), 3.34 (s, 3H), 3.32 (s, 3H), 3.25 (d, J=5.1 Hz, 2H), 2.91-2.85 (m, 2H), 2.68-2.62 (m, 2H), 1.79-1.03 (m, 10H), 1.56 (t, J=7.4 Hz, 3H), a ˜1:1 mixture of rotamers is observed.

後処理

  1. washwashed with saturated sodium hydrogen carbonate (20 mL)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto afford crude product
  6. customThe crude product was purified by flash silica chromatography, elution gradient 0-70% ethyl acetate in isohexane

出典と根拠

ORDレコード
ord-752f319f69cf41cea1a1243f19a3d437
出典データセット
uspto-grants-2011_09
特許番号
US08017602B2

反応ノート

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