Acetic Anhydride → 5-Bromo-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid [1-cyclopropyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-amide

HRID 1480141ノート

反応式

HRID 1480141 の反応式
[CH:1]1([C:4]([NH:10][C:11]([C:13]2[CH:18]=[C:17]([O:19][CH2:20][C:21]([F:24])([F:23])[F:22])[C:16]([Br:25])=[CH:15][N:14]=2)=[O:12])([C:6](=[NH:9])[NH:7][OH:8])[CH3:5])[CH2:3][CH2:2]1.[CH2:26](N(CC)CC)[CH3:27].C(OC(=O)C)(=O)C>CN(C=O)C>[CH:1]1([C:4]([NH:10][C:11]([C:13]2[CH:18]=[C:17]([O:19][CH2:20][C:21]([F:24])([F:22])[F:23])[C:16]([Br:25])=[CH:15][N:14]=2)=[O:12])([C:6]2[N:9]=[C:26]([CH3:27])[O:8][N:7]=2)[CH3:5])[CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 178464905HCID 178464905、化合物

生成物 1

HCID 902039835-Bromo-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid [1-cyclopropyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-amide収率 58.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 5-Bromo-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid [1-cyclopropyl-1-(N-hydroxycarbamimidoyl)-ethyl]-amide (Example 78f, 800 mg, 1.88 mmol) in dry DMF (10 ml) was added triethylamine (190 mg, 262 μl, 1.88 mmol) followed by addition of acetic anhydride (192 mg, 1.88 mmol). The reaction mixture was stirred at room temperature for 1 hours and was then stirred at 125° C. for 30 min under microwave radiation. DMF was removed in vacuo and the residue was dissolved in ethylacetate which was extracted with an 1.0M aqueous solution of sodium bicarbonate. The organic phase was dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a heptane/ethylacetate gradient to yield the title compound (492 mg, 47%) as a light yellow oil. MS (ESI, m/z): 449.3 (M+H+).

後処理

  1. stirringwas then stirred at 125° C. for 30 min under microwave radiation
  2. customDMF was removed in vacuo
  3. dissolutionthe residue was dissolved in ethylacetate which
  4. extractionwas extracted with an 1.0M aqueous solution of sodium bicarbonate
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. customevaporated down to dryness
  7. customThe crude material was purified by flash chromatography on silica eluting with a heptane/ethylacetate gradient

出典と根拠

ORDレコード
ord-1f56f3d0f9c445b09e67a649a856ee01
出典データセット
uspto-grants-2016_08
特許番号
US09409866B2

反応ノート

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