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

HRID 1958336노트

반응식

HRID 1958336 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

실험 절차

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+].

후처리

  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

출처 및 근거

ORD 기록
ord-49790991f5054f039226de6d663fb53f
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410117B2

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