4-Methylmorpholine → 2-Benzoylamino-4-methylthiazole-5-carboxylic Acid (1-Phenylpropyl)amide

HRID 45367

反応式

HRID 45367 の反応式
[C:1]([NH:9][C:10]1[S:11][C:12]([C:16]([OH:18])=O)=[C:13]([CH3:15])[N:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CCOCC1.C(OC(Cl)=O)C(C)C.[CH2:34]([CH:36]([NH2:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH3:35]>O1CCCC1>[C:37]1([CH:36]([NH:43][C:16]([C:12]2[S:11][C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[N:14][C:13]=2[CH3:15])=[O:18])[CH2:34][CH3:35])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

参加物

6

反応物 4

HCID 79724-MethylmorpholineHCID 180541-Phenylpropan-1-amineHCID 62365Isobutyl chloroformateHCID 8568022-Benzoylamino-4-methyl-thiazole-5-carboxylic acid

生成物 1

HCID 593696422-Benzoylamino-4-methylthiazole-5-carboxylic Acid (1-Phenylpropyl)amide収率 19%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-benzoylamino-4-methylthiazole-5-carboxylic acid (0.13 g, 0.50 mmol) and 4-methylmorpholine (0.08 mL, 0.70 mmol) in tetrahydrofuran (20 mL) at 0° C. was added iso-butylchloroformate (0.08 mL, 0.60 mmol). The reaction mixture was stirred for 15 minutes, then warmed to ambient temperature and stirred for another hour before α-ethylbenzylamine (0.1 mL, 0.70 mmol) was added. The reaction mixture was kept stirring at ambient temperature overnight and then concentrated. Purification of the residue by column chromatography afforded the title compound in 19% yield (0.037 g); m. p. 87-89° C.; 1H NMR (CDCl3, 300 MHz) δ 7.89-7.86 (m, 2H), 7.61-7.22 (m, 8H), 5.91 (d, J=7.5 Hz, 1H), 5.02-4.94 (m, 1H), 2.33 (s, 3H), 2.27-1.78 (m, 2H), 0.92 (t, J=7.5 Hz, 3H); 13C NMR (CDCl3, 75 MHz) δ 165.1, 161.4, 157.0, 152.1, 141.8, 133.3, 131.4, 129.1, 128.7, 127.6, 127.5, 126.6, 118.8, 55.6, 29.3, 16.7, 10.8. MS (ES+) m/z 380.5 (M+1).

後処理

  1. additionwas added
  2. stirringThe reaction mixture was kept stirring at ambient temperature overnight
  3. concentrationconcentrated
  4. customPurification of the residue by column chromatography

出典と根拠

ORDレコード
ord-2feb64882ea748ea87061f021f6721bf
出典データセット
uspto-grants-2013_09
特許番号
US08541457B2

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