3-Pyridinecarbonyl chloride, hydrochloride (1:1) → [4-(3-Pyridylcarbonylamino)-2-(2-methylphenyl)benzoyl]methionine Methyl Ester

HRID 2121229노트

반응식

HRID 2121229 반응식
[CH3:1][O:2][C:3](=[O:26])[C@H:4]([CH2:22][CH2:23][S:24][CH3:25])[NH:5][C:6](=[O:21])[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20].Cl.[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[N:31][CH:30]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:26])[C@H:4]([CH2:22][CH2:23][S:24][CH3:25])[NH:5][C:6](=[O:21])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:28]([C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)=[O:35])=[CH:9][C:8]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20]

참가 물질

5

반응물 3

HCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 20622819[4-Amino-2-(2-methylphenyl)benzoyl]methionine methyl ester

생성물 1

HCID 59926755[4-(3-Pyridylcarbonylamino)-2-(2-methylphenyl)benzoyl]methionine Methyl Ester수율 80%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a stirred solution of the [4-amino-2-(2-methylphenyl)benzoyl]methionine methyl ester (85 mg, 0.23 mmol) in CH2Cl2 (5 mL) was added nicotinic acid chloride hydrochloride (81 mg, 0.46 mmol) and saturated NaHCO3 (2 mL). The reaction was stirred at ambient temperature for 2 hours. The reaction was diluted with CH2Cl2 (10 mL), the layers were separated and the organic layer washed with saturated aqueous NaHCO3 (5 mL), dried (MgSO4) and concentrated in vacuo. Flash chromatography (CH2Cl2-methanol 50:1) and crystallization from ethyl acetate gave the desired compound (87 mg, 80%) as a white powder. 1H NMR (300 MHz, CDCl3) δ 9.10 (dd, 1H, J=2.4, 1.0 Hz), 8.80 (dd, 1H, J=4.7, 1.7 Hz), 8.21 (ddd, 1H, J=7.8, 2.4, 1.7 Hz), 8.09-8.00 (m, 2H), 7.71-7.66 (m, 1H), 7.64-7.61 (m, 1H), 7.46 (ddd, 1H, J=7.8, 4.7, 1.0 Hz), 7.35-7.20 (m, 4H), 5.92 (bd, J=7.5 Hz), 4.67-4.57 (m, 1H), 3.66 (s, 3H), 2.23-2.01 (4 s and m, 8H), 2.00 (m, 1H), 1.65-1.52 (m, 1H). MS m/z 478 (M+1)+.

후처리

  1. customthe layers were separated
  2. washthe organic layer washed with saturated aqueous NaHCO3 (5 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customFlash chromatography (CH2Cl2-methanol 50:1) and crystallization from ethyl acetate

출처 및 근거

ORD 기록
ord-5ac6a4109b1a4bd0b9289040838e7114
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06693123B2

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