Benzylamine → N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acid

HRID 45309

반응식

HRID 45309 반응식
[NH2:1][C:2]1[S:3][C:4]([C:8]([OH:10])=O)=[C:5]([CH3:7])[N:6]=1.C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[CH2:43]([NH2:50])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>CN(C)C=O.C(OCC)(=O)C>[CH2:43]([NH:50][C:8]([C:4]1[S:3][C:2]([NH2:1])=[N:6][C:5]=1[CH3:7])=[O:10])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

참가 물질

8

반응물 5

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 8322432-Amino-4-methyl-thiazole-5-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

생성물 1

HCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acid수율 60%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a suspension of 2-amino-4-methylthiazole-5-carboxylic acid (5.20 g, 32.90 mmol) and di-iso-propylethylamine (15.00 mL, 86.70 mmol) in N,N-dimethylformamide (40 mL) was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (8.18 g, 42.70 mmol). The resulting mixture was stirred for 30 min, then 1-hydroxybenzotriazole hydrate (5.78 g, 42.70 mmol) was added, and followed by the addition of benzylamine (4.30 mL, 39.30 mmol). The reaction mixture was stirred at ambient temperature for 2 days, then diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography to afford the title compound in 60% yield (4.90 g); 1H NMR (DMSO-d6, 300 MHz) δ 7.36-7.25 (m, 5H), 5.79 (s, br, 1H), 5.36 (s, br, 2H), 4.54 (dd, J=5.7 Hz, 2H), 2.47 (s, 3H). MS (ES+) m/z 248.4 (M+1).

후처리

  1. stirringThe reaction mixture was stirred at ambient temperature for 2 days
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-476286ae868f46708d1dc3df5cca8daf
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541457B2

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