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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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1,2-Dimethoxyethane → (S)-isopropyl (1-(3-(2-methoxy-6-methylpyridin-3-yl)imidazo[1,2-b]pyridazin-6-yl)pyrrolidin-3-yl)(methyl)carbamate

HRID 870780
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HRID 870780 반응식
[CH:1]([O:4][C:5](=[O:23])[N:6]([C@H:8]1[CH2:12][CH2:11][N:10]([C:13]2[CH:14]=[CH:15][C:16]3[N:17]([C:19](Br)=[CH:20][N:21]=3)[N:18]=2)[CH2:9]1)[CH3:7])([CH3:3])[CH3:2].[CH3:24][O:25][C:26]1[C:31](B(O)O)=[CH:30][CH:29]=[C:28]([CH3:35])[N:27]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].COCCOC>CCOC(C)=O.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].O>[CH:1]([O:4][C:5](=[O:23])[N:6]([C@H:8]1[CH2:12][CH2:11][N:10]([C:13]2[CH:14]=[CH:15][C:16]3[N:17]([C:19]([C:31]4[C:26]([O:25][CH3:24])=[N:27][C:28]([CH3:35])=[CH:29][CH:30]=4)=[CH:20][N:21]=3)[N:18]=2)[CH2:9]1)[CH3:7])([CH3:3])[CH3:2]
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참가 물질

8

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HCID 80711,2-DimethoxyethaneHCID 62657Potassium Phosphate, TribasicHCID 27631212-Methoxy-6-methylpyridine-3-boronic acidHCID 86696483(S)-isopropyl (1-(3-bromoimidazo[1,2-b]pyridazin-6-yl)pyrrolidin-3-yl)(methyl)carbamate

생성물 1

HCID 86696489(S)-isopropyl (1-(3-(2-methoxy-6-methylpyridin-3-yl)imidazo[1,2-b]pyridazin-6-yl)pyrrolidin-3-yl)(methyl)carbamate
수율 54.9%

시약·촉매·용매 3

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

To 80 mg (0.217 mmol) of (S)-isopropyl(1-(3-bromoimidazo[1,2-b]pyridazin-6-yl)pyrrolidin-3-yl)(methyl)carbamate in a microwave vial was added, 54 mg (0.326 mmol) of (2-methoxy-6-methylpyridin-3-yl)boronic acid, 92 mg (0.435 mmol) of K3PO4, 18 mg (0.022 mmol) PdCl2(dppf)2, 3 mL of DME and then 1 mL water. The resulting mixture was microwaved at 140° C. for 0.5 hr. It was diluted with EtOAc, washed with brine, and the organic layer was dried over MgSO4. It was concentrated and purified on the neutral PREP HPLC to obtain 50.6 mg of the desired product. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.30 (d, J=6.32 Hz, 6H) 2.13-2.31 (m, 2H) 2.53 (s, 3H) 2.89 (s, 3H) 3.43 (dd, J=10.61, 7.07 Hz, 1H) 3.49-3.56 (m, 1H) 3.70-3.76 (m, 2H) 4.06 (s, 3H) 4.99 (m, 2H) 6.61 (d, J=9.85 Hz, 1H) 6.89 (d, J=7.83 Hz, 1H) 7.79 (d, J=9.85 Hz, 1H) 8.12 (s, 1H) 8.69 (d, J=7.83 Hz, 1H). LRMS (ESI) m/e 425 [(M+H)+, calcd for C22H28N6O3 424].

후처리

  1. customThe resulting mixture was microwaved at 140° C. for 0.5 hr
  2. washwashed with brine
  3. dry with materialthe organic layer was dried over MgSO4
  4. concentrationIt was concentrated
  5. custompurified on the neutral PREP HPLC

출처 및 근거

ORD 기록
ord-9ada7da08d704948a88a3ac4299df449
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08969565B2

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