Water → 6-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid (2-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-amide

HRID 1958336

反応式

HRID 1958336 の反応式
C[Al](C)C.[C:5]1([C:11]2[N:12]=[C:13]3[N:18]=[C:17]([NH2:19])[CH:16]=[CH:15][N:14]3[CH:20]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C([O:23][C:24]([C:26]1[C:31]([NH:32][C:33]2[CH:34]=[N:35][CH:36]=[N:37][CH:38]=2)=[CH:30][CH:29]=[C:28]([CH:39]2[CH2:41][CH2:40]2)[N:27]=1)=O)C.O>O1CCOCC1.ClCCl.CO>[C:5]1([C:11]2[N:12]=[C:13]3[N:18]=[C:17]([NH:19][C:24]([C:26]4[C:31]([NH:32][C:33]5[CH:38]=[N:37][CH:36]=[N:35][CH:34]=5)=[CH:30][CH:29]=[C:28]([CH:39]5[CH2:40][CH2:41]5)[N:27]=4)=[O:23])[CH:16]=[CH:15][N:14]3[CH:20]=2)[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

参加物

8

反応物 4

HCID 962WaterHCID 16682925TrimethylaluminumHCID 508783902-Phenylimidazo[1,2-A]pyrimidin-7-amineHCID 583680566-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid ethyl ester

生成物 1

HCID 534680246-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid (2-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-amide収率 56%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

実験手順

Trimethylaluminum (2M solution in toluene, 0.26 ml) was added to a stirred suspension of 2-phenyl-imidazo[1,2-a]pyrimidin-7-ylamine (example 1, step 1, 111 mg) in dioxane (5 ml), and the mixture was stirred for 2 h at RT. 6-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid ethyl ester (50 mg) was then added in one portion, and the mixture was heated to 100° C. for 17 h. Upon cooling, water (0.5 ml) was added, followed by small amounts of methanol and dichloromethane to get an almost clear solution. Some Mg504 was added, the mixture was stirred for 15 min, and filtered. The filtrate was concentrated, and the title compound (44 mg, 56%) was isolated from the residue by column chromatography (silica gel, dichloromethane/methanol gradient), followed by trituration (methanol). MS (m/e)=449.2 [M+H+].

後処理

  1. temperaturethe mixture was heated to 100° C. for 17 h
  2. temperatureUpon cooling
  3. customto get an almost clear solution
  4. additionSome Mg504 was added
  5. stirringthe mixture was stirred for 15 min
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated

出典と根拠

ORDレコード
ord-49790991f5054f039226de6d663fb53f
出典データセット
uspto-grants-2013_04
特許番号
US08410117B2

関連ノート

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