Triethylamine → HCID 58746173, 화합물

HRID 724295

반응식

HRID 724295 반응식
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[OH:8].C(N(CC)CC)C.[F:16][C:17]1[CH:18]=[N:19][C:20]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([S:33][CH3:34])[CH:28]=2)=[C:21]([CH:25]=1)[C:22](O)=[O:23].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[F:16][C:17]1[CH:18]=[N:19][C:20]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([S:33][CH3:34])[CH:28]=2)=[C:21]([CH:25]=1)[C:22]([NH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[OH:8])=[O:23]

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6542151cis-2-AminocyclohexanolHCID 113918232-[3-(Methylsulfanyl)phenoxy]-5-fluoronicotinic acid

생성물 1

HCID 58746173HCID 58746173, 화합물수율 58%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

cis-2-Amino-cyclohexane-1-ol (85 mg, 0.56 mmol) and triethylamine (225 μl, 1.61 mmol) were dissolved in dimethylformamide (225 μl) and a solution of 5-fluoro-2-(3-methylsulfanyl-phenoxy)-nicotinic acid (150 mg, 0.54 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (113 mg, 0.59 mmol) and 1-hydroxybenzotriazole (80 mg, 0.59 mmol) in dimethylformamide (5 ml) was added. The reaction was stirred under nitrogen at room temperature for 64 h and the solvent was removed under reduced pressure. The residue was partitioned between 0.5N HCl (10 ml) and ethyl acetate (10 ml) and the aqueous phase was extracted with ethyl acetate (2×10 ml). The combined organic phases were washed with brine (10 ml), dried over MgSO4 and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with pentane:ethyl acetate (70:30, by volume). The product was triturated with pentane (3 ml) to give 5-fluoro-N-[cis-2-hydroxy-cyclohexyl]-2-(3-methylsulfanyl-phenoxy)-nicotinamide (118 mg) as a white solid.

후처리

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was partitioned between 0.5N HCl (10 ml) and ethyl acetate (10 ml)
  3. extractionthe aqueous phase was extracted with ethyl acetate (2×10 ml)
  4. washThe combined organic phases were washed with brine (10 ml)
  5. dry with materialdried over MgSO4
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel eluting with pentane:ethyl acetate (70:30, by volume)
  8. customThe product was triturated with pentane (3 ml)

출처 및 근거

ORD 기록
ord-6c995a5600674bae9e4410236b244145
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141586B2

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