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

HRID 579443ノート

反応式

HRID 579443 の反応式
[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

参加物

9

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-9fb8210d67924352a8980bdf2c07171b
出典データセット
uspto-grants-2015_05
特許番号
US09040714B2

反応ノート

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