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Dimethylformamide → tert-butyl 1-(2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-1-oxopropan-2-ylcarbamate

HRID 512888
ノート
印刷プレビュー

反応式

HRID 512888 の反応式
[N:1]([CH2:4][CH2:5][CH2:6][C:7]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[NH:11][N:10]=[C:9]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])[S:8]1)=[N+:2]=[N-:3].[C:26]([O:30][C:31](C(C)C(O)=O)=[O:32])([CH3:29])([CH3:28])[CH3:27].CCN=C=NC[CH2:44][CH2:45][N:46](C)C.C1C=CC2N(O)N=NC=2C=1.CN([CH:62]=[O:63])C>>[N:1]([CH2:4][CH2:5][CH2:6][C:7]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:11]([C:62](=[O:63])[CH:45]([NH:46][C:31](=[O:32])[O:30][C:26]([CH3:27])([CH3:28])[CH3:29])[CH3:44])[N:10]=[C:9]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])[S:8]1)=[N+:2]=[N-:3]
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 5

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 178517023-(Tert-butoxy)-2-methyl-3-oxopropanoic acidHCID 866048312-(3-Azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazole

生成物 1

HCID 86604830
tert-butyl 1-(2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-1-oxopropan-2-ylcarbamate
収率 94%

反応条件

温度
23 °C

実験手順

2-(3-Azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazole (50 mg, 0.139 mmol; as prepared in example 70) was dissolved in 2.0 mL of DMF. 2-(tert-Butoxycarbonyl) propanoic acid (39 mg, 0.208 mmol), EDCI (40 mg, 0.208 mmol), HOBt (28 mg, 0.208 mmol) and TEA (0.058 mL, 0.417 mmol) were then added and the reaction allowed to stir at 23° C. Following 12 hours, the reaction was quenched by addition of saturated NaHCO3 solution, extracted (3×15 mL ethyl acetate), combined organics washed with water (1×50 mL) then dried over Na2SO4, and concentrated in vacuo. The crude reaction was purified by chromatography (20% ethyl acetate/Hex) affording the product as a white foam (70 mg, 94%). MS APCI (−) m/z 529 (M−1) detected; 1H NMR (400 MHz, CDCl3) δ 7.59 (m, 1H), 7.43 (m, 2H), 7.37 (t, 2H, J=8 Hz), 7.30 (m, 1H), 7.12 (m, 2H), 5.23 (brs, 0.5H), 5.12 (brs, 0.5H), 3.44 (m, 2H), 3.19 (m, 1H), 2.47 (m, 1H), 1.57 (d, 2H, J=9 Hz), 1.43 (m, 12H), 0.89 (m, 1H).

後処理

  1. customthe reaction was quenched by addition of saturated NaHCO3 solution
  2. extractionextracted (3×15 mL ethyl acetate)
  3. washcombined organics washed with water (1×50 mL)
  4. dry with materialthen dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude reaction
  7. customwas purified by chromatography (20% ethyl acetate/Hex)

出典と根拠

ORDレコード
ord-ee7712e842c9481999a4e6891713c6c9
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09102639B2

反応ノート

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