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Sodium Carbonate → HCID 178432609, 화합물

HRID 1530630
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인쇄 미리보기

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HRID 1530630 반응식
Br[C:2]1[CH:3]=[N:4][N:5]([CH3:19])[C:6]=1[CH:7]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8]1.[CH3:20][C:21]1[N:25]=[C:24]([C:26]2[N:27]=[C:28]3[N:38]([CH:39]=2)[CH2:37][CH2:36][O:35][C:34]2[C:29]3=[CH:30][CH:31]=[C:32](B3OC(C)(C)C(C)(C)O3)[CH:33]=2)[N:23]([CH:49]([CH3:51])[CH3:50])[N:22]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:15]([O:14]1[CH2:8][CH:7]([C:6]2[N:5]([CH3:19])[N:4]=[CH:3][C:2]=2[C:32]2[CH:33]=[C:34]3[C:29](=[CH:30][CH:31]=2)[C:28]2[N:38]([CH:39]=[C:26]([C:24]4[N:23]([CH:49]([CH3:50])[CH3:51])[N:22]=[C:21]([CH3:20])[N:25]=4)[N:27]=2)[CH2:37][CH2:36][O:35]3)[CH2:11][CH2:10][NH:9][C:12]1=[O:13])([CH3:18])([CH3:17])[CH3:16]
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참가 물질

6

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HCID 10340Sodium CarbonateHCID 582043852-(2-Isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-8-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azuleneHCID 68313064tert-butyl 3-(4-bromo-1-methyl-1H-pyrazol-5-yl)pyrrolidine-1-carboxylate

생성물 1

HCID 178432609HCID 178432609, 화합물수율 46%

시약·촉매·용매 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

A mixture of tert-butyl 3-(4-bromo-1-methyl-1H-pyrazol-5-yl)pyrrolidine-1-carboxylate (1.0 g, 3.1 mmol), 4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-12-(tetramethyl-1,3,2-dioxaborolan-2-yl)-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1 (14),2,4,10,12-pentaene (1.1 g, 2.5 mmol), Pd(dppf)Cl2 (310 mg, 0.379 mmol), and Na2CO3 (1.34 g, 12.6 mmol) in dioxane (20 mL) was stirred at 80° C. for 16 h. The resultant mixture was extracted with ethyl acetate (50 mL), washed with brine, dried over MgSO4, filtered, and evaporated to afford the crude product, which was purified by reverse phase Combiflash eluting with a 0-70% gradient of CH3CN in 0.3% NH4HCO3 to give 1-tert-butyl-6-(1-methyl-4-{4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-12-yl}-1H-pyrazol-5-yl)-λ3,3-oxazepan-2-one (920 mg, 46% yield) as white solid. LCMS (ESI) m/z: 559.4 [M+H+]. 1H-NMR (500 MHz, DMSO-d6) δ 8.41 (d, J=8.5 Hz, 1H), 7.91 (s, 1H), 7.48 (s, 1H), 7.09 (d, J=8.5 Hz, 1H), 6.96 (s, 1H), 5.88-5.85 (m, 1H), 4.53 (s, 4H), 3.75 (s, 3H), 3.72 (s, 1H), 3.60 (s, 1H), 3.51-3.42 (m, 2H), 3.24-3.20 (m, 1H), 2.26 (s, 3H), 2.15-2.07 (m, 2H), 1.46 (s, 6H), 1.37 (s, 9H).

후처리

  1. extractionThe resultant mixture was extracted with ethyl acetate (50 mL)
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto afford the crude product, which
  7. customwas purified by reverse phase Combiflash
  8. washeluting with a 0-70% gradient of CH3CN in 0.3% NH4HCO3

출처 및 근거

ORD 기록
ord-13f5d3b2f1aa4f6eaa742a7e52356ebb
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09090628B2

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