Methyl 4-Formylbenzoate → Methyl 4-([[2-(4-morpholinyl)ethyl][2-[4-[[4-(2-oxazolyl)phenyl]methyl]phenoxy]ethyl]amino]-methyl]benzoate

HRID 16532ノート

反応式

HRID 16532 の反応式
[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[CH:30]=[CH:29][C:16]([O:17][CH2:18][CH2:19][NH:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[CH:15][CH:14]=2)=[CH:8][CH:7]=1.[CH:31]([C:33]1[CH:42]=[CH:41][C:36]([C:37]([O:39][CH3:40])=[O:38])=[CH:35][CH:34]=1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.O>[N:23]1([CH2:22][CH2:21][N:20]([CH2:31][C:33]2[CH:42]=[CH:41][C:36]([C:37]([O:39][CH3:40])=[O:38])=[CH:35][CH:34]=2)[CH2:19][CH2:18][O:17][C:16]2[CH:15]=[CH:14][C:13]([CH2:12][C:9]3[CH:10]=[CH:11][C:6]([C:2]4[O:1][CH:5]=[CH:4][N:3]=4)=[CH:7][CH:8]=3)=[CH:30][CH:29]=2)[CH2:24][CH2:25][O:26][CH2:27][CH2:28]1

参加物

6

反応物 3

HCID 15294Methyl 4-FormylbenzoateHCID 5049666Sodium triacetoxyborohydrideHCID 68488020N-[2-[4-[[4-(2-oxazolyl)phenyl]methyl]phenoxy)ethyl]-4-morpholineethanamine

生成物 1

HCID 68484695Methyl 4-([[2-(4-morpholinyl)ethyl][2-[4-[[4-(2-oxazolyl)phenyl]methyl]phenoxy]ethyl]amino]-methyl]benzoate収率 84%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 63651,1-Dichloroethane溶媒

実験手順

A solution of N-[2-[4-[[4-(2-oxazolyl)phenyl]methyl]phenoxy]ethyl]-4-morpholineethanamine (0.25 g, 0.6 mmol) and methyl 4-formylbenzoate (0.11 g, 0.66 mmol) in dichloroethane (5 mL) was stirred as sodium triacetoxyborohydride (0.16 g, 0.74 mmol) was added and stirred for 17 h. The reaction was diluted with water and extracted with ethyl acetate. The combined organic extracts were dried and concentrated. Purification by chromatography on silica gel using a gradient of methanol in dichloromethane gave 0.28 g of methyl 4-[[[2-(4-morpholinyl)ethyl][2-[4-[[4-(2-oxazolyl)phenyl]methyl]phenoxy]ethyl]amino]-methyl]benzoate; 1H NMR (400 MHz, CDCl3) δ 7.97 (m, 4H), 7.68 (s, 1H), 7.42 (d, 2H), 7.27 (d, 2H), 7.21 (s, 1H), 7.08 (d, 2H), 6.78 (d, 2H), 4.03 (t, 2H), 3.96 (s, 2H), 3.92 (s, 3H), 3.79 (s, 2H), 3.66 (m, 4H), 2.92 (t, 2H), 2.73 (t, 2H), 2.47 (m, 2H), 2.42 (m, 4H) ppm.

後処理

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated
  5. customPurification by chromatography on silica gel using a gradient of methanol in dichloromethane

出典と根拠

ORDレコード
ord-9cb967a7307141fe8cbfef16effb9564
出典データセット
uspto-grants-2010_06
特許番号
US07737145B2

反応ノート

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