4-Ethylbenzoyl chloride → 4-Ethyl-N-[[2-[(3S)-3-methyl-2,6-dioxopiperidin-3-YL]-1,3-dioxoisoindolin-5-YL]methyl]benzamide

HRID 331549

반응식

HRID 331549 반응식
[CH2:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)[CH3:2].Cl.[NH2:13][CH2:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[C:20](=[O:24])[N:19]([C@@:25]1([CH3:33])[CH2:30][CH2:29][C:28](=[O:31])[NH:27][C:26]1=[O:32])[C:18]2=[O:34]>C(#N)C>[CH2:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:13][CH2:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[C:20](=[O:24])[N:19]([C@@:25]2([CH3:33])[CH2:30][CH2:29][C:28](=[O:31])[NH:27][C:26]2=[O:32])[C:18]3=[O:34])=[O:8])=[CH:5][CH:4]=1)[CH3:2]

참가 물질

4

반응물 2

HCID 853684-Ethylbenzoyl chlorideHCID 670196915-aminomethyl-2-[(3S)-3-methyl-2,6-dioxo-piperidin-3-yl]-isoindole-1,3-dione hydrochloride

생성물 1

HCID 247883104-Ethyl-N-[[2-[(3S)-3-methyl-2,6-dioxopiperidin-3-YL]-1,3-dioxoisoindolin-5-YL]methyl]benzamide수율 76%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

TEA (0.44 g, 4.4 mmol) was added to a mixture of 4-ethylbenzoyl chloride (0.34 g, 2.0 mmol) and 5-aminomethyl-2-[(3S)-3-methyl-2,6-dioxo-piperidin-3-yl]-isoindole-1,3-dione hydrochloride (0.67 g, 2.0 mmol) in acetonitrile (20 mL). The mixture was stirred at room temperature for 2 hours, and was evaporated under vacuum. The residue was partitioned between water (100 mL) and ethyl acetate (100 mL), and the organic phase was evaporated. The residue was chromatographed on silica gel using ethyl acetate as the mobile phase, providing 0.65 g, in 76% yield. The product was obtained as a white solid; mp 160-162° C.; HPLC, Waters Symmetry C-18, 3.9×150 mm, 5 μm, 1 mL/min, 240 nm, 45/55 CH3CN/0.1% H3PO4, 4.20 (97.47%); 1H NMR (DMSO-d6) δ 1.19 (t, J=7.7 Hz, 3H), 1.89 (s, 3H), 2.02-2.08 (m, 1H), 2.54-2.62 (m, 2H), 2.65-2.78 (m, 3H), 4.61 (d, J=6.0 Hz, 2H), 7.32 (d, J=8.1 Hz, 2H), 7.76-7.84 (m, 5H), 9.14 (t, J=6.0 Hz, 1H), 11.01 (s, 1H); 13C NMR (DMSO-d6) δ 15.4, 21.1, 28.1, 28.6, 29.2, 42.6, 58.8, 121.6, 123.2, 127.4, 127.8, 129.6, 131.4, 131.5, 133.4, 147.6, 147.7, 166.4, 167.8, 167.9, 172.2, 172.3; Anal. Calcd for C24H23N3O5: C, 66.50; H, 5.35; N, 9.69. Found: C, 66.30; H, 5.26; N, 9.56.

후처리

  1. customwas evaporated under vacuum
  2. customThe residue was partitioned between water (100 mL) and ethyl acetate (100 mL)
  3. customthe organic phase was evaporated
  4. customThe residue was chromatographed on silica gel
  5. customproviding 0.65 g
  6. customThe product was obtained as a white solid

출처 및 근거

ORD 기록
ord-f81747485ba94cb49cd5856de0a73fba
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877780B2

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