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

HRID 1914595ノート

反応式

HRID 1914595 の反応式
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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8a72e6a1b1d3470584d88c1e573aeb08
出典データセット
uspto-grants-2013_12
特許番号
US08614209B2

反応ノート

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