Hydrochloric Acid → 3-(4-Trifluoromethylsulfanyl-phenylamino)-isonicotinic acid

HRID 2421751노트

반응식

HRID 2421751 반응식
F[C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[F:11][C:12]([F:22])([F:21])[S:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.Cl>C1COCC1>[F:11][C:12]([S:13][C:14]1[CH:20]=[CH:19][C:17]([NH:18][C:2]2[CH:10]=[N:9][CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])=[CH:16][CH:15]=1)([F:22])[F:21]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 1230544-((Trifluoromethyl)thio)anilineHCID 3453613-Fluoropyridine-4-carboxylic acidHCID 2733832Lithium Hexamethyldisilazide

생성물 1

HCID 576496423-(4-Trifluoromethylsulfanyl-phenylamino)-isonicotinic acid수율 10%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

3-Fluoro-isonicotinic acid (50 mg, 0.354 mmol) and 4-(trifluoromethylthio)aniline (68.5 mg, 0.354 mmol) was added to 2 ml dry THF and the mixture was cooled to −78° C. LiHMDS (1M in THF, 1.24 ml) was added and the mixture was allowed to warm to room temperature over night. Hydrochloric acid (1M in methanol, 5 ml) was added and the volatiles were removed in vacuo. The crude material was purified by preparative HPLC to give 11.4 mg (45 μmol; 10% yield) of pure desired product. LC-MS (method V): rt=3.09 min; m/z [M+H]+ 315.

후처리

  1. temperatureto warm to room temperature over night
  2. customthe volatiles were removed in vacuo
  3. customThe crude material was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-6de2c2f04d604cc4bc7363cb54b357aa
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07956191B2

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