4-Fluorobenzylamine → 2-Bromo-N-(4-fluorobenzyl)-4-methylthiazole-5-carboxamide

HRID 560568

반응식

HRID 560568 반응식
[Br:1][C:2]1[S:3][C:4]([C:8]([OH:10])=O)=[C:5]([CH3:7])[N:6]=1.Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C.ON1C2C=CC=CC=2N=N1.[F:42][C:43]1[CH:50]=[CH:49][C:46]([CH2:47][NH2:48])=[CH:45][CH:44]=1>O1CCCC1>[Br:1][C:2]1[S:3][C:4]([C:8]([NH:48][CH2:47][C:46]2[CH:49]=[CH:50][C:43]([F:42])=[CH:44][CH:45]=2)=[O:10])=[C:5]([CH3:7])[N:6]=1

참가 물질

7

반응물 5

HCID 673264-FluorobenzylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 28240582-Bromo-4-methyl-1,3-thiazole-5-carboxylic acid

생성물 1

HCID 666314052-Bromo-N-(4-fluorobenzyl)-4-methylthiazole-5-carboxamide수율 81%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of of 2-bromo-4-methylthiazole-5-carboxylic acid (2.00 g, 9.00 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.41 g, 12.6 mmol) and N,N-diisopropylethylamine (4.67 mL, 27.0 mmol) in tetrahydrofuran (40 mL) was added 1-hydroxybenzotriazole (1.70 g, 12.6 mmol). The resulting mixture was stirred at ambient temperature for 30 minutes and 4-fluorobenzylamine (1.43 mL, 12.6 mmol) was added. The reaction mixture was kept stirring at ambient temperature for 17 hours, then concentrated in vacuo. The residue was dissolved ethyl acetate and washed with water and brine. The organic solution was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography to afford 2-bromo-N-(4-fluorobenzyl)-4-methylthiazole-5-carboxamide in 81% yield (2.38 g): 1H NMR (300 MHz, CDCl3) δ 7.30-7.26 (m, 2H), 7.05-7.00 (m, 2H), 5.99-5.87 (m, 1H), 4.54 (d, J=5.7 Hz, 2H), 2.63 (s, 3H).

후처리

  1. stirringThe reaction mixture was kept stirring at ambient temperature for 17 hours
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved ethyl acetate
  4. washwashed with water and brine
  5. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-6e61ecc4d4194569a3b2f4a10afdfd05
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063084B2

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