1-Hydroxybenzotriazole hydrate → N-[4-(1-Hydroxy-1-methyl-ethyl)-benzyl]-2-(3-methylsulfanyl-phenoxy)-nicotinamide

HRID 844055

반응식

HRID 844055 반응식
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[O:6][C:7]1[N:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=O.[NH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([OH:30])([CH3:29])[CH3:28])=[CH:23][CH:22]=1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=N)C>CN(C)C=O.O>[OH:30][C:27]([C:24]1[CH:25]=[CH:26][C:21]([CH2:20][NH:19][C:9](=[O:11])[C:8]2[CH:12]=[CH:13][CH:14]=[N:15][C:7]=2[O:6][C:5]2[CH:16]=[CH:17][CH:18]=[C:3]([S:2][CH3:1])[CH:4]=2)=[CH:22][CH:23]=1)([CH3:29])[CH3:28]

참가 물질

7

반응물 4

HCID 27960291-Hydroxybenzotriazole hydrateHCID 101542112-[4-(aminomethyl)phenyl]propan-2-olHCID 218771742-[3-(Methylsulfanyl)phenoxy]nicotinic acidHCID 21883477Ethylcarbodiimide hydrochloride

생성물 1

HCID 22612047N-[4-(1-Hydroxy-1-methyl-ethyl)-benzyl]-2-(3-methylsulfanyl-phenoxy)-nicotinamide수율 14.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution 2-(3-Methylsulfanyl-phenoxy)-nicotinic acid (2.5 grams, 9.58 mmole), 2-(4-Aminomethyl-phenyl)-propan-2-ol (1.896 grams, 11.50 mmole) and 1-hydroxybenzotriazole hydrate (1.55 grams, 11.50 mmole) in dry dimethylformamide (60 ml) was added 1-(3-dimethylamino)-propyl)-3-ethylcarbodiimide hydrochloride (2.39 grams, 12.45 mmole) and stirred over night. The mixture was diluted with 300 ml water and extracted with ethyl acetate. The combined organics were washed with water and brine, dried over MgSO4, filtered and concentrated to give a yellow oil that was purified by chromatography on silica eluting with 3.5% methanol/methylene chloride to give a white solid. Recrystalization from ethyl acetate/hexane gave a solid (0.550 g). M.P. 107-109° C.; Anal. calcd. for C23H24N2O3S: C, 67.62; H, 5.92; N, 6.86. Found: C, 67.53, H, 5.76; N, 6.91.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe combined organics were washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a yellow oil that
  7. customwas purified by chromatography on silica eluting with 3.5% methanol/methylene chloride
  8. customto give a white solid
  9. customRecrystalization from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-61cf55dc6c854cc692ace2654e29efb5
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06380218B1

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