Sodium Carbonate → HCID 136217478、化合物

HRID 1752428ノート

反応式

HRID 1752428 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.[C:11]([C@@H:14]([NH:16][C:17]1[N:22]=[C:21](Cl)[N:20]=[C:19]([C:24]([NH2:26])=[O:25])[CH:18]=1)[CH3:15])(=[O:13])[NH2:12].C([O-])([O-])=O.[Na+].[Na+]>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.O1CCOCC1>[C:11]([C@@H:14]([NH:16][C:17]1[N:22]=[C:21]([C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)[N:20]=[C:19]([C:24]([NH2:26])=[O:25])[CH:18]=1)[CH3:15])(=[O:13])[NH2:12]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 27343604-Hydroxyphenylboronic acidHCID 89422280HCID 89422280、化合物

生成物 1

HCID 136217478HCID 136217478、化合物収率 91.6%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A 100 mL round-bottom flask was charged with 4-hydroxyphenyl boronic acid (1 g, 7.25 mmol), 6-((S)-1-carbamoyl-ethylamino)-2-chloro-pyrimidine-4-carboxylic acid amide (7.25 mmol, 1.76 g), PdCl2(PPh3)2 (Aldrich, 0.5 mmol, 0.3562 g), Na2CO3 (7.25 mL, 2M aqueous solution), and dioxane (5 mL). The flask was purged with nitrogen and heated to 100° C. for 16 h at which time the reaction was complete. The reaction mixture was concentrated under reduced pressure. The residue was suspended in 50% MeOH in DCM, filtered by vacuum, and the filter cake was discarded. The filtrate was concentrated under reduced pressure and was suspended in DCM, stirred for one hour, and filtered by vacuum filtration to provide the title compound as a light brown powder (2 g, 91%). 1H NMR (CD3OD) 8.25-8.09 (m, 2H), 7.09-6.92 (m, 1H), 6.82-6.70 (m, 2H), 4.62-4.40 (m, 1H), 1.49-1.31 (m, 3H). LC/MS: m/z 301[M+H]+.

後処理

  1. customThe flask was purged with nitrogen
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. filtrationfiltered by vacuum
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. filtrationfiltered by vacuum filtration

出典と根拠

ORDレコード
ord-7b5bbcc73bdf44b39dc24999d09baabe
出典データセット
uspto-grants-2015_10
特許番号
US09163008B2

反応ノート

読み込み中…