Triethylamine → N-hydroxy-4-(4-(3-(3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-5-yl)propoxy)phenylsulfonyl)tetrahydro-2H-pyran-4-carboxamide

HRID 2181386노트

반응식

HRID 2181386 반응식
[C:1]([CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([C:17]2([C:23](OC(C)(C)C)=[O:24])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1)(O)=[O:2].O.[OH:31][N:32]1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[F:48][C:49]([F:62])([F:61])[O:50][C:51]1[CH:60]=[CH:59][C:54]([C:55](=[N:57]O)[NH2:56])=[CH:53][CH:52]=1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[OH:31][NH:32][C:23]([C:17]1([S:14]([C:11]2[CH:10]=[CH:9][C:8]([O:7][CH2:6][CH2:5][CH2:4][C:1]3[O:2][N:57]=[C:55]([C:54]4[CH:59]=[CH:60][C:51]([O:50][C:49]([F:62])([F:61])[F:48])=[CH:52][CH:53]=4)[N:56]=3)=[CH:13][CH:12]=2)(=[O:15])=[O:16])[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1)=[O:24]

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27333094-(Trifluoromethoxy)benzamidoximeHCID 27960291-Hydroxybenzotriazole hydrateHCID 865907724-[[4-(3-carboxypropoxy)phenyl]sulfonyl]tetrahydro-2H-pyran-4-carboxylic acid, 1,1-dimethylethyl ester

생성물 1

HCID 22484431N-hydroxy-4-(4-(3-(3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-5-yl)propoxy)phenylsulfonyl)tetrahydro-2H-pyran-4-carboxamide수율 88.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Part A. In dry equipment under nitrogen, 4-[[4-(3carboxypropoxy)phenyl]sulfonyl]tetrahydro-2H-pyran-4-carboxylic acid, 1,1-dimethylethyl ester (2.57 g, 6.0 mmol, prepared as in Example 7) was dissolved in dry N,N-dimethylformamide (12 mL), and the remaining reagents were added to the solution in the following order: 1-hydroxybenzotriazole hydrate (1.13 g, 8.4 mmol), triethylamine (1.0 mL, 7.2 mmol), 4-(trifluoromethoxy)benzamidoxime (1.58 g, 7.2 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.73 g, 9.0 mmol). After 2 hr at 35° C., the reaction was concentrated in vacuo. The residue was taken up in ethyl acetate, washed with water, saturated sodium bicarbonate solution, and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. Purification by flash column chromatography using ethyl acetate/hexanes afforded 3.05 g (81%) of the desired product as a clear glass. ESMS m/z=631 [M+Na]+.

후처리

  1. additionthe remaining reagents were added to the solution in the following order
  2. concentrationthe reaction was concentrated in vacuo
  3. washwashed with water, saturated sodium bicarbonate solution, and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash column chromatography

출처 및 근거

ORD 기록
ord-5a3a713f91d6438eb7176ed7ecdfd66e
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06890928B2

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