Trifluoroacetic acid → 5-(4-Fluorophenyl)-2-({6-[(methylamino)methyl]pyridin-2-yl}amino)thiophene-3-carboxamide

HRID 385776노트

반응식

HRID 385776 반응식
C(O[C:6](=O)[N:7]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][C:17]2[S:18][C:19]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[CH:20][C:21]=2[C:22]([NH2:24])=[O:23])[N:11]=1)C)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[F:31][C:28]1[CH:29]=[CH:30][C:25]([C:19]2[S:18][C:17]([NH:16][C:12]3[CH:13]=[CH:14][CH:15]=[C:10]([CH2:9][NH:7][CH3:6])[N:11]=3)=[C:21]([C:22]([NH2:24])=[O:23])[CH:20]=2)=[CH:26][CH:27]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 59525661tert-Butyl[(6-{[3-(aminocarbonyl)-5-(4-fluorophenyl)-2-thienyl]amino}pyridin-2-yl)methyl]methylcarbamate

생성물 1

HCID 251261625-(4-Fluorophenyl)-2-({6-[(methylamino)methyl]pyridin-2-yl}amino)thiophene-3-carboxamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl[(6-{[3-(aminocarbonyl)-5-(4-fluorophenyl)-2-thienyl]amino}pyridin-2-yl)methyl]methylcarbamate (90 mg, 0.197 mmol) in dichloromethane (0.4 mL) was added trifluoroacetic acid (0.4 mL) and the reaction was maintained at room temperature for 1 hour. The volatiles were removed in vacuo and the crude product was purified by reverse phase HPLC (20-90% acetonitrile/water with 0.05% trifluoroacetic acid). The appropriate fractions were diluted with ethyl acetate (50 mL) and saturated aqueous sodium bicarbonate (40 mL). The layers were separated and the organic layer was washed with saturated aqueous sodium bicarbonate (40 mL) and water (2×40 mL), dried over sodium sulfate, filtered and concentrated to yield the title compound.

후처리

  1. customThe volatiles were removed in vacuo
  2. customthe crude product was purified by reverse phase HPLC (20-90% acetonitrile/water with 0.05% trifluoroacetic acid)
  3. additionThe appropriate fractions were diluted with ethyl acetate (50 mL) and saturated aqueous sodium bicarbonate (40 mL)
  4. customThe layers were separated
  5. washthe organic layer was washed with saturated aqueous sodium bicarbonate (40 mL) and water (2×40 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-03c2f1ac3eee4d9e95faa0a7079af875
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367706B2

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