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Dimethylformamide → (S)-3-((5-((6-Bromobenzo[d]thiazol-2-yl)methyl)-1,3,4-oxadiazol-2-yl)amino)pyrrolidin-2-one

HRID 1754257
ノート
印刷プレビュー

反応式

HRID 1754257 の反応式
[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([CH2:9][C:10]3[O:14][C:13](O)=[N:12][N:11]=3)[S:8][C:4]=2[CH:3]=1.CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.[N:34]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:38]2C=C[CH:41]=[CH:42][C:37]=2[N:36]=N1.CN(C=[O:58])C>CCOC(C)=O>[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([CH2:9][C:10]3[O:14][C:13]([NH:36][C@H:37]4[CH2:42][CH2:41][NH:34][C:38]4=[O:58])=[N:12][N:11]=3)[S:8][C:4]=2[CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 1785189165-((6-Bromobenzo[d]thiazol-2-yl)methyl)-1,3,4-oxadiazol-2-ol

生成物 1

HCID 90047760(S)-3-((5-((6-Bromobenzo[d]thiazol-2-yl)methyl)-1,3,4-oxadiazol-2-yl)amino)pyrrolidin-2-one収率 50%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
35 °C

実験手順

To a solution of Compound 51a (145 mg, 0.47 mmol) in DMF (4 mL) was added DIEA (0.243 mL, 1.39 mmol) followed by (S)-3-aminopyrrolidin-2-one, HCl (70 mg, 0.51 mmol). To the stirring solution was added BOP (247 mg, 0.56 mmol) and the reaction mixture stirred at 35° C. for 18 h. The reaction mixture was diluted with EtOAc and the solution washed with saturated NH4Cl. The aqueous portion was washed with EtOAc, and the combined organic extracts washed with brine. The organic portion was dried (Na2SO4), filtered and concentrated under reduced pressure then the residue purified on silica gel chromatography eluting with 0.5 to 12% MeOH to give Compound 51b (92 mg, 50% yield) as a light orange solid. LCMS=0.75 min using analytical method (M), 396.0 (M+H). 1H NMR (400 MHz CDCl3 containing CD3OD) δ 8.02 (d, J=1.8 Hz, 1H), 7.82 (d, J=8.8 Hz, 1H), 7.58 (dd, J=8.7, 1.9 Hz, 1H), 4.26 (dd, J=10.4, 8.4 Hz, 1H), 3.43-3.38 (m, 1H), 2.68 (dddd, J=12.6, 8.3, 6.1, 2.0 Hz, 1H), 2.18-1.96 (m, 1H).

後処理

  1. washthe solution washed with saturated NH4Cl
  2. washThe aqueous portion was washed with EtOAc
  3. washthe combined organic extracts washed with brine
  4. dry with materialThe organic portion was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customthe residue purified on silica gel chromatography
  8. washeluting with 0.5 to 12% MeOH

出典と根拠

ORDレコード
ord-e5fb79b413e245e0adeea13c36034b38
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09169240B2

反応ノート

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