PyBroP → Tert-butyl 3-(2-((2,6-bis(trifluoromethyl)quinolin-4-yl)amino)acetamido)azetidine-1-carboxylate

HRID 1896834노트

반응식

HRID 1896834 반응식
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:12]=[C:11](O)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[N:4]=1.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[NH2:44][CH2:45][C:46]([NH:48][CH:49]1[CH2:52][N:51]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH2:50]1)=[O:47]>O1CCOCC1>[F:1][C:2]([F:19])([F:18])[C:3]1[CH:12]=[C:11]([NH:44][CH2:45][C:46]([NH:48][CH:49]2[CH2:52][N:51]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH2:50]2)=[O:47])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[N:4]=1

참가 물질

5

반응물 3

HCID 2733179PyBroPHCID 18699815Tert-butyl 3-(2-aminoacetamido)azetidine-1-carboxylateHCID 1785161332,6-Bis(trifluoromethyl)quinolin-4(1H)-one

생성물 1

HCID 86660461Tert-butyl 3-(2-((2,6-bis(trifluoromethyl)quinolin-4-yl)amino)acetamido)azetidine-1-carboxylate

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

실험 절차

A solution of commercially available 2,6-bis(trifluoromethyl)quinolin-4-ol (291 mg, 1.04 mmol) in dry dioxane (5 mL) was treated sequentially with TEA (0.36 mL, 2.58 mmol) and PyBrOP (586 mg, 1.26 mmol). After stirring 1 hour at room temperature under argon, a solution of tert-butyl 3-(2-aminoacetamido)azetidine-1-carboxylate (352, 1.54 mmol), prepared as described in Example 1, Step E in dry dioxane (5 mL) was introduced and the reaction mixture was stirred overnight at room temperature. After concentration in vacuo, the residue was purified by flash chromatography (silica gel, 0-5% MeOH/ethyl acetate) to afford the product.

후처리

  1. additionwas introduced
  2. stirringthe reaction mixture was stirred overnight at room temperature
  3. concentrationAfter concentration in vacuo
  4. customthe residue was purified by flash chromatography (silica gel, 0-5% MeOH/ethyl acetate)
  5. customto afford the product

출처 및 근거

ORD 기록
ord-eb44cbf949534acbac30b55cb8526b6e
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08518969B2

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