Acetic Acid → HCID 68728792, 화합물

HRID 452999노트

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HRID 452999 반응식
[NH2:1][C:2]1[CH:13]=[C:6]2[C:7]([O:9]C(=O)[NH:11][C:5]2=[CH:4][CH:3]=1)=O.C(N(CC)CC)C.[CH2:21]([O:28][CH2:29][C:30](Cl)=[O:31])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl.[NH2:34][CH:35]1[CH2:40][CH2:39][C:38](=[O:41])[NH:37][C:36]1=[O:42].C(O)(=O)C>O>[NH2:11][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:30](=[O:31])[CH2:29][O:28][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:13][C:6]=1[C:7]([NH:34][CH:35]1[CH2:40][CH2:39][C:38](=[O:41])[NH:37][C:36]1=[O:42])=[O:9]

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 8471Triethylamine2회HCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 177085Benzyloxyacetyl chlorideHCID 27353536-Amino-2-hydroxy-4H-3,1-benzoxazin-4-one

생성물 1

HCID 68728792HCID 68728792, 화합물수율 12.2%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

To a stirred mixture of 5-amino-isatoic anhydride (1.0 g, 5.6 mmol) and triethyl amine (0.8 mL, 9.0 mmol) in acetronitrile (15 mL), was added benzyloxyacetyl chloride (0.87 mL, 5.6 mmol) dropwise at room temperature. The mixture was kept at room temperature overnight. To the mixture, was added triethylamine (3.1 mL, 22 mmol), 3-amino-piperidine-2,6-dione hydrogen chloride (0.92 g, 5.6 mmol), and acetic acid (3.2 mL, 56 mmol). The mixture was heated at 80° C. for 8 hours. To the mixture, was added water (75 mL). The suspension was filtered and washed with water (75 mL) and ethyl acetate (75 mL) to give a dark solid, which was purified with column chromatography (Silica Gel, methanol/methylene chloride 0% to 10% in 15 min) to give 2-amino-5-(2-benzyloxy-acetylamino)-N-(2,6-dioxo-piperidin-3-yl)-benzamide as a white solid (0.28 g, 12% yield): 1H NMR (DMSO-d6) δ 1.92-2.18 (m, 2H, 2CHH), 2.50-2.55 (m, 1H, CHH), 2.72-2.84 (m, 1H, C H), 4.03 (s, 2H, CH2), 4.61 (s, 2H, CH2), 4.68-4.77 (m, 1H, NCH), 6.19 (br, 2H, NH2), 6.68 (d, J=9 Hz, 1H, Ar), 7.30-7.42 (m, 6H, Ar), 7.62 (d, J=2 Hz, 1H, Ar), 8.43 (d, J=8 Hz, 1H, NH), 9.44 (s, 1H, NH), 10.84 (s, 1H, NH); 13C NMR (DMSO-d6) δ 24.09, 30.96, 49.12, 69.37, 72.35, 114.27, 116.23, 121.11, 125.99, 126.13, 127.64, 127.77, 128.27, 137.68, 146.19, 167.28, 168.36, 172.35, 173.01.

후처리

  1. filtrationThe suspension was filtered
  2. washwashed with water (75 mL) and ethyl acetate (75 mL)
  3. customto give a dark solid, which
  4. customwas purified with column chromatography (Silica Gel, methanol/methylene chloride 0% to 10% in 15 min)

출처 및 근거

ORD 기록
ord-9dde7c0582e748e6a1fb6ef6dedb6512
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492395B2

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