Diisopropylethylamine → (4,4-Difluoro-azepan-1-yl)-(5-oxazol-4-yl-thiophen-3-yl)-methanone

HRID 1914595

반응식

HRID 1914595 반응식
FC(F)(F)C(O)=O.[F:8][C:9]1([F:16])[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[O:17]1[CH:21]=[C:20]([C:22]2[S:26][CH:25]=[C:24]([C:27](O)=[O:28])[CH:23]=2)[N:19]=[CH:18]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1.C(Cl)Cl>[F:8][C:9]1([F:16])[CH2:15][CH2:14][CH2:13][N:12]([C:27]([C:24]2[CH:23]=[C:22]([C:20]3[N:19]=[CH:18][O:17][CH:21]=3)[S:26][CH:25]=2)=[O:28])[CH2:11][CH2:10]1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 581102215-Oxazol-4-yl-thiophene-3-carboxylic acidHCID 668498474,4-Difluoro-azepane trifluoroacetate

생성물 1

HCID 44226481(4,4-Difluoro-azepan-1-yl)-(5-oxazol-4-yl-thiophen-3-yl)-methanone수율 30.9%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

4,4-Difluoro-azepane trifluoroacetate (Synthesis 47, 0.113 g, 0.45 mmol) was dissolved in THF (1 mL) and added to 5-oxazol-4-yl-thiophene-3-carboxylic acid (0.059 g, 0.30 mmol). DIPEA (0.154 mL, 0.90 mmol) was added followed by HATU (0.125 g, 0.33 mmol) and the reaction mixture was then stirred at room temperature overnight. The mixture was diluted with DCM then washed with aqueous sodium carbonate solution. The organics were dried over sodium sulfate, filtered and evaporated. The crude material was purified by HPLC, eluting with 5%-98% methanol in water (0.1% formic acid). The fractions containing the desired product were freeze-dried to give the title compound (0.029 g). LCMS m/z 313.15 [m+H]+ R.T.=8.31 min (Analytical Method 10).

후처리

  1. washthen washed with aqueous sodium carbonate solution
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude material was purified by HPLC
  6. washeluting with 5%-98% methanol in water (0.1% formic acid)
  7. additionThe fractions containing the desired product
  8. customwere freeze-dried

출처 및 근거

ORD 기록
ord-8a72e6a1b1d3470584d88c1e573aeb08
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08614209B2

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