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 340832노트

반응식

HRID 340832 반응식
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]([C:17](=[CH2:21])C(O)=O)[CH:7]=1.C1C=CC2N([OH:31])N=NC=2C=1.CNC[C:35]1[O:36][C:37]2[CH:44]=[CH:43][CH:42]=[CH:41][C:38]=2[C:39]=1C.[CH2:45]([N:47]([CH:51](C)C)[CH:48]([CH3:50])C)C>CN(C=O)C.O>[CH3:51][N:47]([CH2:48][C:50]1[O:36][C:37]2[CH:44]=[CH:43][CH:42]=[CH:41][C:38]=2[C:39]=1[CH3:35])[C:45](=[O:31])[CH:21]=[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

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 46785639N-methyl-1-(3-methylbenzofuran-2-yl)methanamineHCID 1317320875,7,8,9-Tetrahydro-6-oxa-1,9-diaza-benzocyclohepten-3-yl-acrylic acid hydrochloride

생성물 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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
35 °C

실험 절차

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. lire 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 (3.0 mL), stirred for 20 mm then filtered to give a beige solid as a mixture of amide rotaruers. Yield: 0.10 g (62%); 1H NMR (300 MHz, DMSO-d6) δ8.25 (s, 1H), 7.94 (s, 1H), 7.59-7.03 (m, 6H), 6.79 (hr 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]+

후처리

  1. temperaturewas 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 (3.0 mL)
  6. stirringstirred for 20 mm
  7. filtrationthen filtered
  8. customto give a beige solid

출처 및 근거

ORD 기록
ord-88e98d1462714e8cb54d5d2150daed46
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895545B2

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