Trifluoroacetic acid → 1-amino-N-{6-[(3,3-dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-3-pyridinyl}cyclobutanecarboxamide

HRID 527556노트

반응식

HRID 527556 반응식
[CH3:1][C:2]1([CH3:33])[C:6]2[C:7]([O:11][C:12]3[N:17]=[CH:16][C:15]([NH:18][C:19]([C:21]4([NH:25]C(=O)OC(C)(C)C)[CH2:24][CH2:23][CH2:22]4)=[O:20])=[CH:14][CH:13]=3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1.C(O)(C(F)(F)F)=O>ClCCl>[NH2:25][C:21]1([C:19]([NH:18][C:15]2[CH:16]=[N:17][C:12]([O:11][C:7]3[C:6]4[C:2]([CH3:33])([CH3:1])[CH2:3][O:4][C:5]=4[CH:10]=[CH:9][CH:8]=3)=[CH:13][CH:14]=2)=[O:20])[CH2:24][CH2:23][CH2:22]1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 866984251,1-Dimethylethyl {1-[({6-[(3,3-dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-3-pyridinyl}amino)carbonyl]cyclobutyl}carbamate2회

생성물 1

HCID 679668331-amino-N-{6-[(3,3-dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-3-pyridinyl}cyclobutanecarboxamide수율 98.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1,1-dimethylethyl {1-[({6-[(3,3-dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-3-pyridinyl}amino)carbonyl]cyclobutyl}carbamate (Intermediate 69, 23.5 mg) in dry dichloromethane (3.5 ml), TFA (159 μl, 2.07 mmol) was slowly added at 0° C. and the reaction mixture was stirred for 2 hours at room temperature. The solvent and the excess of TFA were evaporated and the residue was purified with an SCX cartridge. The cartridge was washed with 3 CV of methanol, then the compound was adsorbed on the cartridge, washed with 5 CV of methanol and desorbed with 2 CV of methanolic ammonia (1N). This afforded the title compound (18 mg).

후처리

  1. customThe solvent and the excess of TFA were evaporated
  2. customthe residue was purified with an SCX cartridge
  3. washThe cartridge was washed with 3 CV of methanol
  4. washwashed with 5 CV of methanol

출처 및 근거

ORD 기록
ord-bbd71462a9944b6e8ff517bb539987fc
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346790B2

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