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Triethylamine → 6-phenoxy-2-(3-{5-[1-(2-pyrrolidin-1-ylethyl)-1H-pyrazol-4-yl]-pyrimidin-2-yl}benzyl)-2H-pyridazin-3-one

HRID 532419
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HRID 532419 반응식
Br[C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:9]=[C:10]([CH:26]=[CH:27][CH:28]=2)[CH2:11][N:12]2[C:17](=[O:18])[CH:16]=[CH:15][C:14]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:13]2)=[N:6][CH:7]=1.[N:29]1([CH2:34][CH2:35][N:36]2[CH:40]=[C:39](B3OC(C)(C)C(C)(C)O3)[CH:38]=[N:37]2)[CH2:33][CH2:32][CH2:31][CH2:30]1.O.O.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(N(CC)CC)C>COCCOC.CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[O:19]([C:14]1[CH:15]=[CH:16][C:17](=[O:18])[N:12]([CH2:11][C:10]2[CH:26]=[CH:27][CH:28]=[C:8]([C:5]3[N:4]=[CH:3][C:2]([C:39]4[CH:38]=[N:37][N:36]([CH2:35][CH2:34][N:29]5[CH2:33][CH2:32][CH2:31][CH2:30]5)[CH:40]=4)=[CH:7][N:6]=3)[CH:9]=2)[N:13]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
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참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 18407952Tripotassium phosphate trihydrateHCID 584970712-[3-(5-bromopyrimidin-2-yl)benzyl]-6-phenoxy-2H-pyridazin-3-oneHCID 588858611-(2-(pyrrolidin-1-yl)ethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

생성물 1

HCID 468365016-phenoxy-2-(3-{5-[1-(2-pyrrolidin-1-ylethyl)-1H-pyrazol-4-yl]-pyrimidin-2-yl}benzyl)-2H-pyridazin-3-one

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매HCID 80711,2-Dimethoxyethane용매

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온도
85 °C

실험 절차

3.5 A suspension of 218 mg (0.50 mmol) of 2-[3-(5-bromopyrimidin-2-yl)benzyl]-6-phenoxy-2H-pyridazin-3-one, 251 mg (0.75 mmol) of 1-(2-pyrrolidin-1-ylethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (content 87%) and 230 mg (1.00 mmol) of tripotassium phosphate trihydrate in 2 ml of 1,2-dimethoxyethane and 1 ml of DMF is heated to 85° C. under nitrogen. 35.0 mg (0.05 mmol) of bis(triphenylphosphine)palladium(II) chloride and 9 μl (0.07 mmol) of triethylamine are then added and stirred at 85° C. for 42 hours. The reaction mixture is partitioned between THF and saturated sodium chloride solution. The organic phase is dried over sodium sulfate, evaporated and chromatographed on a silica-gel column with methanol/tert-butyl ether as eluent, giving 6-phenoxy-2-(3-{5-[1-(2-pyrrolidin-1-ylethyl)-1H-pyrazol-4-yl]-pyrimidin-2-yl}benzyl)-2H-pyridazin-3-one as yellowish amorphous material; ESI 520.

후처리

  1. customThe reaction mixture is partitioned between THF and saturated sodium chloride solution
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customevaporated
  4. customchromatographed on a silica-gel column with methanol/tert-butyl ether as eluent

출처 및 근거

ORD 기록
ord-48c076e405a34fb0a7ca9242fbafce0e
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08853211B2

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