Triethylamine → HCID 1120195、化合物

HRID 1818074ノート

反応式

HRID 1818074 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2([CH2:16][NH2:17])[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(N(CC)CC)C.[O:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[CH:27]=[C:26]1[C:34](Cl)=[O:35]>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2([CH2:16][NH:17][C:34]([C:26]3[O:25][C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=4[CH:27]=3)=[O:35])[CH2:12][CH2:13][CH2:14][CH2:15]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 389492-Benzofurancarbonyl chlorideHCID 739193STK362959

生成物 1

HCID 1120195HCID 1120195、化合物収率 78%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

C-[1-(3,4-Dimethoxy-phenyl)-cyclopentyl]-methylamine (141 mg, 0.600 mmol) was dissolved in anhydrous 1,4-dioxane (2 mL) containing triethylamine (167 μL, 1.20 mmol). Benzofuran -2-carbonyl chloride (108 mg, 0.600 mmol) was then added and the reaction mixture was allowed to stir for 16 hours. The reaction mixture was filtered, evaporated to dryness, and purified by column chromatography on silica gel using a gradient of 5-50% ethyl acetate in hexanes. The pure fractions were combined and evaporated to dryness to yield a white solid (0.1775 g, 0.4678 mmol, 78.0%) ESI-MS m/z calc. 379.5, found 380.2 (M+1)+. Retention time of 3.36 minutes. 1H NMR (400 MHz, DMSO-d6) δ 1.57-2.03 (m, 8H), 3.46 (d, J=6.4 Hz, 2H), 3.72 (s, 6H), 6.81-6.89 (m, 3H), 7.31 (t, J=7.5 Hz, 1H), 7.44 (t, J=7.8 Hz, 1H), 7.48 (s, 1H), 7.60 (d, J=8.4 Hz, 1H), 7.75 (d, J=8.4 Hz, 1H), 7.94 (t, J=6.3 Hz, 1H). 13C NMR (100 MHz, DMSO-d6) δ 23.1, 35.3, 47.2, 51.8, 55.5, 109.2, 111.5, 111.6, 111.7, 118.8, 122.6, 123.6, 126.7, 127.1, 139.3, 147.1, 148.3, 149.1, 154.1, 158.2.

後処理

  1. filtrationThe reaction mixture was filtered
  2. customevaporated to dryness
  3. custompurified by column chromatography on silica gel using a gradient of 5-50% ethyl acetate in hexanes
  4. customevaporated to dryness

出典と根拠

ORDレコード
ord-1059de7be54140e3a6d2c7cb49b67dc2
出典データセット
uspto-grants-2009_10
特許番号
US07598412B2

反応ノート

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