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Sodium Carbonate → HCID 59379868、化合物

HRID 2353712
ノート
印刷プレビュー

反応式

HRID 2353712 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.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
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 4

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

生成物 1

HCID 59379868HCID 59379868、化合物

試薬・触媒・溶媒 2

HCID 178418476
HCID 178418476、化合物
触媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

[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).

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. customwere evaporated to dryness
  6. customThe crude product was further purified by preparative HPLC

出典と根拠

ORDレコード
ord-ab112ebc83604480a1cbd366c0e17bc8
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

読み込み中…

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