Trifluoroacetic acid → HCID 68487554, 화합물

HRID 1875181노트

반응식

HRID 1875181 반응식
CC([N:5]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([O:17][C:18]2[CH:23]=[C:22]([CH:24]3[CH2:26][CH2:25]3)[CH:21]=[C:20]([C:27]#[N:28])[CH:19]=2)[C:11]=1[F:29])C(=O)[O-])(C)C.C(O)(C(F)(F)F)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl.CCOC(C)=O>[NH2:5][CH2:9][C:10]1[C:11]([F:29])=[C:12]([O:17][C:18]2[CH:19]=[C:20]([CH:21]=[C:22]([CH:24]3[CH2:25][CH2:26]3)[CH:23]=2)[C:27]#[N:28])[C:13]([Cl:16])=[CH:14][CH:15]=1

참가 물질

6

반응물 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86761654HCID 86761654, 화합물

생성물 1

HCID 68487554HCID 68487554, 화합물수율 89%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 1,1-dimethylethyl({4-chloro-3-[(3-cyano-5-cyclopropylphenyl)oxy]-2-fluorophenyl}methyl)carbamate (880 mg, 2.111 mmol) dissolved in DCM (15 ml) was added TFA (5.0 ml) and the reaction mixture was stirred for 30 minutes at RT. The reaction mixture was neutralized with saturated sodium bicarbonate, diluted with EtOAc, and the organics layer was separated. The solvent was evaporated and the crude material was purifed via silica gel chromatography to give 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-cyclopropylbenzonitrile (594 mg, 1.875 mmol, 89% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.38-7.52 (m, 2H), 7.22 (s, 1H), 7.04 (d, 2H), 3.73 (s, 2H), 1.91-2.01 (m, 1H), 1.89 (br. s., 2H), 0.89-1.04 (m, 2H), 0.64-0.81 (m, 2H).

후처리

  1. customthe organics layer was separated
  2. customThe solvent was evaporated

출처 및 근거

ORD 기록
ord-05aeee70b58041aebe21529220920975
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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