Potassium Carbonate → HCID 178502349, 화합물

HRID 1751424노트

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HRID 1751424 반응식
Br[C:2]1[CH:3]=[C:4]2[C:31](=[CH:32][CH:33]=1)[C:8]1[NH:9][C:10]([C@@H:12]3[CH2:16][CH2:15][CH2:14][N:13]3[C:17](=[O:30])[C@@H:18]([NH:25][C:26](=[O:29])[O:27][CH3:28])[CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[N:11][C:7]=1[CH2:6][CH2:5]2.CC1(C)C(C)(C)OB([C:42]2[CH:43]=[C:44]3[C:49](=[CH:50][CH:51]=2)[CH:48]=[C:47]([C:52]2[NH:56][C:55]([C@@H:57]4[CH2:61][CH2:60][CH2:59][N:58]4[C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])=[N:54][CH:53]=2)[CH:46]=[CH:45]3)O1.C([O-])([O-])=O.[K+].[K+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:28][O:27][C:26]([NH:25][C@@H:18]([CH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)[C:17]([N:13]1[CH2:14][CH2:15][CH2:16][C@H:12]1[C:10]1[NH:9][C:8]2[C:31]3[C:4]([CH2:5][CH2:6][C:7]=2[N:11]=1)=[CH:3][C:2]([C:42]1[CH:43]=[C:44]2[C:49](=[CH:50][CH:51]=1)[CH:48]=[C:47]([C:52]1[NH:56][C:55]([C@@H:57]4[CH2:61][CH2:60][CH2:59][N:58]4[C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])=[N:54][CH:53]=1)[CH:46]=[CH:45]2)=[CH:33][CH:32]=3)=[O:30])=[O:29]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 584986761,1-Dimethylethyl (2S)-2-[5-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthalenyl]-1H-imidazol-2-yl]-1-pyrrolidinecarboxylateHCID 178502347HCID 178502347, 화합물

생성물 1

HCID 178502349HCID 178502349, 화합물수율 40%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

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온도
85 °C

실험 절차

Methyl (S)-2-((S)-2-(7-bromo-4,5-dihydro-1H-naphtho[1,2-d]imidazol-2-yl)pyrrolidin-1-yl)-2-oxo-1-(tetrahydro-2H-pyran-4-yl)ethylcarbamate (211 mg, 0.408 mmol), (S)-tert-butyl 2-(5-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (220 mg, 0.449 mmol), Pd(PPh3)4 (47 mg, 0.0408 mmol) and K2CO3 (2M in H2O, 0.45 mL, 0.9 mmol) were suspended in DME (4 mL). The reaction mixture was degassed for 10 min with N2 then heated to 85° C. After 17 h, it was cooled to RT, diluted with MeOH, filtered over a thiol SPE column and concentrated. The crude residue was purified by silica column chromatography (0% to 40% MeOH/EtOAc) to afford the title compound (130 mg, 40%).

후처리

  1. customThe reaction mixture was degassed for 10 min with N2
  2. temperatureit was cooled to RT
  3. additiondiluted with MeOH
  4. filtrationfiltered over a thiol SPE column
  5. concentrationconcentrated
  6. customThe crude residue was purified by silica column chromatography (0% to 40% MeOH/EtOAc)

출처 및 근거

ORD 기록
ord-0298525bd7f64d26855f9324bbdd4756
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156823B2

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