Triethylamine → 7Hydroxy-4-methyl-3-[4-methyl-5-(4-methyl-piperazine-1-carbonyl)-thiazol-2-yl]-chromen-2-one

HRID 579443노트

반응식

HRID 579443 반응식
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH2:8](N(CC)CC)C.[OH:15][C:16]1[CH:25]=[C:24]2[C:19]([CH:20]=[C:21]([C:27]3[S:28][C:29]([C:33](O)=[O:34])=[C:30]([CH3:32])[N:31]=3)[C:22](=[O:26])[O:23]2)=[CH:18][CH:17]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C([O-])(O)=O.[Na+]>O.O1CCCC1>[OH:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20]([CH3:8])=[C:21]([C:27]3[S:28][C:29]([C:33]([N:5]4[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]4)=[O:34])=[C:30]([CH3:32])[N:31]=3)[C:22](=[O:26])[O:23]2)=[CH:18][CH:17]=1

참가 물질

9

반응물 6

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 1363877702-(7-Hydroxy-2-oxo-2H-chromen-3-yl)-4-methyl-thiazole-5-carboxylic acid

생성물 1

HCID 1363877737Hydroxy-4-methyl-3-[4-methyl-5-(4-methyl-piperazine-1-carbonyl)-thiazol-2-yl]-chromen-2-one수율 83.7%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To dry tetrahydrofuran (12 mL) at 0° C., 1-methylpiperazine (61 μL, 55 mg, 0.55 mmol), triethylamine (210 μL, 152 mg, 1.5 mmol), 2-(7-hydroxy-2-oxo-2H-chromen-3-yl)-4-methyl-thiazole-5-carboxylic acid (156 mg, 0.49 mmol), (3-dimethylamino-propyl)-ethyl-carbodiimid hydrochloride (105 mg, 0.55 mmol) and 1-hydroxybenzotriazole monohydrate (84 mg, 0.55 mmol) were added sequentially, and the mixture was stirred at room temperature for 16 h. After addition of water (30 mL) the pH was adjusted to 8 by addition of a 5% aqueous solution of NaHCO3 and the mixture was extracted with tetrahydrofuran (3×15 mL). After drying (MgSO4) and evaporation, the residue was purified by column chromatography over silica (Kieselgel 60) using chloroform-methanol 9:1 as eluent. The title compound (156 mg, 0.41 mmol, 81%) was obtained as a yellow solid.

후처리

  1. extractionthe mixture was extracted with tetrahydrofuran (3×15 mL)
  2. customAfter drying
  3. custom(MgSO4) and evaporation
  4. customthe residue was purified by column chromatography over silica (Kieselgel 60)

출처 및 근거

ORD 기록
ord-9fb8210d67924352a8980bdf2c07171b
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040714B2

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