1,2-Dichloroethane → N-Methyl-N-(3-methyl-benzofuran-2-ylmethyl)-3-(5,7,8,9-tetrahydro-6-oxa-1,9-diaza-benzocyclohepten-3-yl)-acrylamide

HRID 1879979ノート

反応式

HRID 1879979 の反応式
C(Cl)CCl.Cl.[N:6]1[C:11]2[NH:12][CH2:13][CH2:14][O:15][CH2:16][C:10]=2[CH:9]=[C:8]([CH:17]=[CH:18][C:19]([OH:21])=O)[CH:7]=1.C1C=CC2N(O)N=NC=2C=1.[CH3:32][NH:33][CH2:34][C:35]1[O:36][C:37]2[CH:44]=[CH:43][CH:42]=[CH:41][C:38]=2[C:39]=1[CH3:40].C(N(C(C)C)C(C)C)C>CN(C=O)C.O>[CH3:32][N:33]([CH2:34][C:35]1[O:36][C:37]2[CH:44]=[CH:43][CH:42]=[CH:41][C:38]=2[C:39]=1[CH3:40])[C:19](=[O:21])[CH:18]=[CH:17][C:8]1[CH:7]=[N:6][C:11]2[NH:12][CH2:13][CH2:14][O:15][CH2:16][C:10]=2[CH:9]=1

参加物

8

反応物 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 46785639N-methyl-1-(3-methylbenzofuran-2-yl)methanamineHCID 684149593-(5,7,8,9-Tetrahydro-6-oxa-1,9-diaza-benzocyclohepten-3-yl)-acrylic acid hydrochloride

生成物 1

HCID 68413589N-Methyl-N-(3-methyl-benzofuran-2-ylmethyl)-3-(5,7,8,9-tetrahydro-6-oxa-1,9-diaza-benzocyclohepten-3-yl)-acrylamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
35 °C

実験手順

EDC (0.10 g, 0.52 mmol) was added to a solution of 3-(5,7,8,9-Tetrahydro-6-oxa-1,9-diaza-benzocyclohepten-3-yl)-acrylic acid hydrochloride (0.11 g, 0.43 mmol), HOBt (64 mg, 0.47 mmol), Methyl-(3-methyl-benzofuran-2-ylmethyl)-amine (91 mg, 0.52 mmol) and (i-Pr)2EtN (0.44 mL, 2.58 mmol) in DMF (6 mL). The mixture was allowed to stir overnight at 35° C. The mixture was cooled to 0° C. and diluted with H2O (15 mL) with rapid stirring. The resulting precipitate was filtered, washed with H2O (30 mL) then dried under high vacuum. The solid was triturated with Et2O (30 mL), stirred for 20 min then filtered to give a beige solid as a mixture of amide rotamers. Yield: 0.10 g (62%); 1H NMR (300 MHz, DMSO-d6) δ 8.25 (s, 1H), 7.94 (s, 1H), 7.59-7.03 (m, 6H), 6.79 (br s, 1H), 4.98 and 4.79 (2×s, 2H), 4.53 (s, 2H), 3.77-3.73 (m, 2H), 3.25-3.19 (m, 2H), 3.17 and 2.93 (2×s, 3H), 2.28 (s, 3H); ESI MS m/z 378 [C22H23N3O3+H]+

後処理

  1. temperatureThe mixture was cooled to 0° C.
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with H2O (30 mL)
  4. customthen dried under high vacuum
  5. customThe solid was triturated with Et2O (30 mL)
  6. stirringstirred for 20 min
  7. filtrationthen filtered
  8. customto give a beige solid

出典と根拠

ORDレコード
ord-18e7ecc7747249699e9178e9e306cc70
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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