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Sodium Carbonate → HCID 59380007, 화합물

HRID 2353711
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HRID 2353711 반응식
[CH:1]1([NH:4][C:5](=[O:16])[NH:6][C:7]2[CH:12]=[CH:11][C:10](B(O)O)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].Cl[C:24]1[N:29]=[C:28]([CH2:30][S:31]([CH:34]2[CH2:36][CH2:35]2)(=[O:33])=[O:32])[CH:27]=[C:26]([N:37]2[CH2:42][CH2:41][O:40][CH2:39][C@@H:38]2[CH3:43])[N:25]=1>CN(C=O)C.COCCOC.C(O)C.O.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>[CH:1]1([NH:4][C:5](=[O:16])[NH:6][C:7]2[CH:12]=[CH:11][C:10]([C:24]3[N:29]=[C:28]([CH2:30][S:31]([CH:34]4[CH2:36][CH2:35]4)(=[O:32])=[O:33])[CH:27]=[C:26]([N:37]4[CH2:42][CH2:41][O:40][CH2:39][C@@H:38]4[CH3:43])[N:25]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 57427756[4-(3-Cyclopropylureido)phenyl]boronic acidHCID 59380174HCID 59380174, 화합물

생성물 1

HCID 59380007HCID 59380007, 화합물

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 6228
Dimethylformamide
용매
HCID 86587095Dimethoxyethane ethanol water용매

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온도
100 °C

실험 절차

[4-(3-Cyclopropylureido)phenyl]boronic acid, pinacol ester (80 mg, 0.26 mmol), sodium carbonate (1.055 mL, 2.11 mmol), dichlorobis(triphenylphosphine)palladium(II) (14.8 mg, 0.02 mmol) and 2-chloro-4-(cyclopropylsulfonylmethyl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine (70 mg, 0.21 mmol) were suspended in 18% DMF in DME:Ethanol:Water 7:2:3 mixture (4 mL) and sealed into a microwave tube. The reaction was heated to 100° C. for 10 minutes in the microwave reactor and cooled to RT. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M ammonia in methanol. The crude product was further purified by preparative HPLC using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents, to give the desired material as a colourless gum (33.0 mg).

후처리

  1. customsealed into a microwave tube
  2. temperaturecooled to RT
  3. customThe crude product was purified by ion exchange chromatography
  4. washThe desired product was eluted from the column
  5. customThe crude product was further purified by preparative HPLC

출처 및 근거

ORD 기록
ord-492abfbdd61340f59a283f34016485e9
출처 데이터셋
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07750003B2

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