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Sodium Carbonate → HCID 59380007、化合物

HRID 2353711
ノート
印刷プレビュー

反応式

HRID 2353711 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 57427756[4-(3-Cyclopropylureido)phenyl]boronic acidHCID 59380174HCID 59380174、化合物

生成物 1

HCID 59380007HCID 59380007、化合物

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide
溶媒
HCID 86587095Dimethoxyethane ethanol water溶媒

反応条件

温度
100 °C

実験手順

[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).

後処理

  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

出典と根拠

ORDレコード
ord-492abfbdd61340f59a283f34016485e9
出典データセット
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07750003B2

反応ノート

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