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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
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HRID 512888 반응식
[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]
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참가 물질

6

반응물 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

생성물 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
수율 94%

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온도
23 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ee7712e842c9481999a4e6891713c6c9
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09102639B2

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