Triethylamine → HCID 66893244, 화합물

HRID 1479680노트

반응식

HRID 1479680 반응식
[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][C:8]([CH2:12][CH2:13][C:14]3[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][C:15]=3[CH3:23])=[CH:7][C:6]=2[C:5]2[CH:24]=[CH:25][C:26]([CH3:28])=[CH:27][C:4]=2[N:3]=1.C(N(CC)CC)C.[NH2:36][CH2:37][CH2:38][NH:39][C:40](=[O:42])[CH3:41]>CCOCC.C(OCC)(=O)C.O>[C:40]([NH:39][CH2:38][CH2:37][NH:36][C:18](=[O:19])[C:17]1[CH:21]=[CH:22][C:14]([CH2:13][CH2:12][C:8]2[CH:9]=[N:10][C:11]3[C:2]([NH2:1])=[N:3][C:4]4[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][C:5]=4[C:6]=3[CH:7]=2)=[C:15]([CH3:23])[CH:16]=1)(=[O:42])[CH3:41]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 66082N-(2-aminoethyl)acetamideHCID 86652358HCID 86652358, 화합물

생성물 1

HCID 66893244HCID 66893244, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylbenzoyl chloride (Example 116/Step 2) and triethylamine (2.5 eq.) in ether (0.05 M) was added N-(2-aminoethyl)acetamide (5.0 eq.). The reaction mixture was stirred for overnight. Then the reaction mixture was diluted with ethyl acetate and water. The two phases were separated, and the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vaccuo. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-80% ethyl acetate in hexane to give N-(2-acetamidoethyl)-4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylbenzamide as a white solid. 1H NMR (CDCl3): δ 8.61 (s, 1H), 8.38 (s, 1H), 8.07 (d, 1H), 7.65 (s, 1H), 7.51-7.56 (m, 2H), 7.10-7.16 (m, 2H), 6.25 (br, 2H), 3.50-3.59 (m, 4H), 3.08-3.16 (m, 4H), 2.62 (s, 3H), 2.52 (s, 3H), 2.35 (s, 3H). LRMS [M+H]=455.2.

후처리

  1. customThe two phases were separated
  2. extractionthe aqueous layer was extracted twice with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated en vaccuo
  6. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

출처 및 근거

ORD 기록
ord-55b62b9056ed4c93a13cfa01640cb75b
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09408907B2

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