Diisopropylethylamine → N-[4-(1-Hydroxy-1-methyl-ethyl)-cyclohexylmethyl]-2-(3-nitro-phenoxy)-nicotinamide

HRID 844093ノート

反応式

HRID 844093 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[O:7][C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=O)([O-:3])=[O:2].[NH2:20][CH2:21][C@H:22]1[CH2:27][CH2:26][C@H:25]([C:28]([OH:31])([CH3:30])[CH3:29])[CH2:24][CH2:23]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C=O)C.C(OCC)(=O)C>[OH:31][C:28]([CH:25]1[CH2:26][CH2:27][CH:22]([CH2:21][NH:20][C:10](=[O:12])[C:9]2[CH:13]=[CH:14][CH:15]=[N:16][C:8]=2[O:7][C:6]2[CH:17]=[CH:18][CH:19]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH2:23][CH2:24]1)([CH3:30])[CH3:29]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 226123442-(3-Nitro-phenoxy)-nicotinic acidHCID 178459251HCID 178459251、化合物

生成物 1

HCID 22612428N-[4-(1-Hydroxy-1-methyl-ethyl)-cyclohexylmethyl]-2-(3-nitro-phenoxy)-nicotinamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 2-(3-nitro-phenoxy)-nicotinic acid (86.9 mg, 0.33 mmol), trans-2-(4-Aminomethyl-cyclohexyl)-propan-2-ol (57.2 mg, 0.33 mmol), benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (148 mg, 0.33 mmol), and diisopropylethyl amine (0.29 mL, 1.67 mmol) in 10 mL of dry DMF was stirred overnight. The solution was then diluted with ethyl acetate and washed with water, 5% citric acid, saturated sodium bicarbonate, and brine, dried over magnesium sulfate and concentrated to an oil. Purified through a pad of silica eluted with ethyl acetate to give a clear oil (120 mg.) 1HNMR (CDCl3) δ1.04 (4H, dd), 1.14 (6H, s), 1.55 (2 s), 1.88 (4. m), 3.37 (2H, t) 7.23 (1H, m), 7.51 (1H, d), 7.64 (1H, t), 8.07 (1H, t), 8.16 (2H, m), 8.63 (1H, dd); MS: m/e 414 (M++1).

後処理

  1. washwashed with water, 5% citric acid, saturated sodium bicarbonate, and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated to an oil
  4. customPurified through a pad of silica
  5. washeluted with ethyl acetate
  6. customto give a clear oil (120 mg.) 1HNMR (CDCl3) δ1.04 (4H, dd), 1.14 (6H, s), 1.55 (2 s), 1.88 (4. m), 3.37 (2H, t) 7.23 (1H, m), 7.51 (1H, d), 7.64 (1H, t), 8.07 (1H, t), 8.16 (2H, m), 8.63 (1H, dd)

出典と根拠

ORDレコード
ord-5ec5bf75e4dd4992a06d7183b16ea033
出典データセット
uspto-grants-2002_04
特許番号
US06380218B1

反応ノート

読み込み中…