Diisopropylethylamine → (4Z,7Z,10Z,13Z,16Z,19Z)-N-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)docosa-4,7,10,13,16,19-hexaenamide

HRID 573396

반응식

HRID 573396 반응식
[CH:1]1[CH:2]=[C:3]2[C:10](=[O:11])[N:9]([CH:12]3[C:18](=[O:19])[NH:17][C:15](=[O:16])[CH2:14][CH2:13]3)[CH2:8][C:4]2=[C:5]([NH2:7])[CH:6]=1.[C:20](O)(=[O:42])[CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25]/[CH:26]=[CH:27]\[CH2:28]/[CH:29]=[CH:30]\[CH2:31]/[CH:32]=[CH:33]\[CH2:34]/[CH:35]=[CH:36]\[CH2:37]/[CH:38]=[CH:39]\[CH2:40][CH3:41].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CC#N.CCOC(C)=O.CN(C=O)C>[O:19]=[C:18]1[CH:12]([N:9]2[CH2:8][C:4]3[C:3](=[CH:2][CH:1]=[CH:6][C:5]=3[NH:7][C:20](=[O:42])[CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25]/[CH:26]=[CH:27]\[CH2:28]/[CH:29]=[CH:30]\[CH2:31]/[CH:32]=[CH:33]\[CH2:34]/[CH:35]=[CH:36]\[CH2:37]/[CH:38]=[CH:39]\[CH2:40][CH3:41])[C:10]2=[O:11])[CH2:13][CH2:14][C:15](=[O:16])[NH:17]1

참가 물질

8

반응물 4

HCID 81531DiisopropylethylamineHCID 216326LenalidomideHCID 445580DoconexentHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 70945158(4Z,7Z,10Z,13Z,16Z,19Z)-N-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)docosa-4,7,10,13,16,19-hexaenamide수율 63.7%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

Lenalidomide (200 mg, 0.771 mmol) was taken up in 5 mL of CH3CN and 2 mL of DMF along with (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid (DHA, 253 mg, 0.771 mmol), HATU (322 mg, 0.848 mmol) and DIEA (200 μL, 2.3 mmol). The resulting reaction mixture was stirred at room temperature for 3 h and diluted with EtOAc (20 mL). The organic layer was washed with water (3×5 mL), brine, dried (Na2SO4) and concentrated under reduced pressure. Purification by silica gel chromatography (95% CH2Cl2, 5% MeOH) afforded 280 mg of (4Z,7Z,10Z,13Z,16Z,19Z)-N-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)docosa-4,7,10,13,16,19-hexaenamide (63%). MS (EI) calculated for C35H43N3O4: 569.33; found: [M+H]+ 570.

후처리

  1. customThe resulting reaction mixture
  2. washThe organic layer was washed with water (3×5 mL), brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customPurification by silica gel chromatography (95% CH2Cl2, 5% MeOH)

출처 및 근거

ORD 기록
ord-9f63894673be47dd8594244af616f9da
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029548B2

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