Trifluoroacetic anhydride → 5-(3,5-dichloro-phenyl)-3-[4-(1H-pyrazol-4-yl)-naphthalen-1-yl]-5-trifluoromethyl-4,5-dihydro-isoxazole

HRID 388371노트

반응식

HRID 388371 반응식
FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(OC([N:21]1[CH:25]=[C:24]([C:26]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:29]([C:36]3[CH2:40][C:39]([C:45]4[CH:50]=[C:49]([Cl:51])[CH:48]=[C:47]([Cl:52])[CH:46]=4)([C:41]([F:44])([F:43])[F:42])[O:38][N:37]=3)=[CH:28][CH:27]=2)[CH:23]=[N:22]1)=O)(C)(C)C.[OH-].[Na+]>ClCCl>[Cl:51][C:49]1[CH:50]=[C:45]([C:39]2([C:41]([F:43])([F:42])[F:44])[O:38][N:37]=[C:36]([C:29]3[C:30]4[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:26]([C:24]4[CH:23]=[N:22][NH:21][CH:25]=4)=[CH:27][CH:28]=3)[CH2:40]2)[CH:46]=[C:47]([Cl:52])[CH:48]=1

참가 물질

5

반응물 3

HCID 9845Trifluoroacetic anhydrideHCID 14798Sodium HydroxideHCID 674362084-{4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-naphthalen-1-yl}-pyrazole-1-carboxylic acid tert-butyl ester

생성물 1

HCID 468423985-(3,5-dichloro-phenyl)-3-[4-(1H-pyrazol-4-yl)-naphthalen-1-yl]-5-trifluoromethyl-4,5-dihydro-isoxazole

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Trifluoroacetic acid anhydride (0.18 ml) is added to a solution of 4-{4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-naphthalen-1-yl}-pyrazole-1-carboxylic acid tert-butyl ester (135 mg) in dichloromethane (1 ml). After 1 hour at room temperature an aqueous solution of sodium hydroxide (30%) is added. The aqueous phase is extracted with dichloromethane and the combined organic phases are dried over MgSO4 and concentrated in vacuo. The crude product is purified on a semi-preparative HPLC to yield 5-(3,5-dichloro-phenyl)-3-[4-(1H-pyrazol-4-yl)-naphthalen-1-yl]-5-trifluoromethyl-4,5-dihydro-isoxazole as a colorless solid: m.p. 117-120° C. (compound 1.17, table 1).

후처리

  1. extractionThe aqueous phase is extracted with dichloromethane
  2. dry with materialthe combined organic phases are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product is purified on a semi-preparative HPLC

출처 및 근거

ORD 기록
ord-52533b5a58f746f1b3004fb65bc8ec0d
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08377942B2

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