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

HRID 844093노트

반응식

HRID 844093 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-5ec5bf75e4dd4992a06d7183b16ea033
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06380218B1

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