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Sodium Carbonate → HCID 59379868, 화합물

HRID 2353712
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HRID 2353712 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.Cl[C:18]1[N:23]=[C:22]([C:24]([S:27]([CH:30]2[CH2:32][CH2:31]2)(=[O:29])=[O:28])([CH3:26])[CH3:25])[CH:21]=[C:20]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][C@@H:34]2[CH3:39])[N:19]=1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC.O.CCO>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>[CH:1]1([NH:4][C:5](=[O:16])[NH:6][C:7]2[CH:12]=[CH:11][C:10]([C:18]3[N:23]=[C:22]([C:24]([S:27]([CH:30]4[CH2:31][CH2:32]4)(=[O:28])=[O:29])([CH3:26])[CH3:25])[CH:21]=[C:20]([N:33]4[CH2:38][CH2:37][O:36][CH2:35][C@@H:34]4[CH3:39])[N:19]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 57427756[4-(3-Cyclopropylureido)phenyl]boronic acidHCID 59380019HCID 59380019, 화합물HCID 86587095Dimethoxyethane ethanol water

생성물 1

HCID 59379868HCID 59379868, 화합물

시약·촉매·용매 2

HCID 178418476
HCID 178418476, 화합물
촉매
HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

[4-(3-Cyclopropylureido)phenyl]boronic acid, pinacol ester (199 mg, 0.66 mmol), 2-chloro-4-(2-cyclopropylsulfonylpropan-2-yl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine (190 mg, 0.53 mmol), sodium carbonate (1.320 mL, 2.64 mmol) and dichlorobis(triphenylphosphine)palladium(II) (37.1 mg, 0.05 mmol) were suspended in 18% DMF in a DME:Water:EtOH 7:3:2 solution (4 mL) and sealed into a microwave tube. The reaction was heated to 100° C. for 20 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 and pure fractions were evaporated to dryness. 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 white solid (85 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. customwere evaporated to dryness
  6. customThe crude product was further purified by preparative HPLC

출처 및 근거

ORD 기록
ord-ab112ebc83604480a1cbd366c0e17bc8
출처 데이터셋
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07750003B2

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