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

HRID 45367

반응식

HRID 45367 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-2feb64882ea748ea87061f021f6721bf
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541457B2

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