Morpholine → 2-[(4-{2-[(5-Ethylpyrimidin-2-yl)(4-morpholin-4-ylbenzyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester

HRID 914497ノート

反応式

HRID 914497 の反応式
C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+].[C:28]([O:32][C:33](=[O:62])[C:34]([S:37][C:38]1[S:39][CH:40]=[C:41]([CH2:43][CH2:44][N:45]([CH2:54][C:55]2[CH:60]=[CH:59][C:58](Br)=[CH:57][CH:56]=2)[C:46]2[N:51]=[CH:50][C:49]([CH2:52][CH3:53])=[CH:48][N:47]=2)[N:42]=1)([CH3:36])[CH3:35])([CH3:31])([CH3:30])[CH3:29].[NH:63]1[CH2:68][CH2:67][O:66][CH2:65][CH2:64]1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:28]([O:32][C:33](=[O:62])[C:34]([S:37][C:38]1[S:39][CH:40]=[C:41]([CH2:43][CH2:44][N:45]([C:46]2[N:51]=[CH:50][C:49]([CH2:52][CH3:53])=[CH:48][N:47]=2)[CH2:54][C:55]2[CH:60]=[CH:59][C:58]([N:63]3[CH2:68][CH2:67][O:66][CH2:65][CH2:64]3)=[CH:57][CH:56]=2)[N:42]=1)([CH3:36])[CH3:35])([CH3:31])([CH3:30])[CH3:29]

参加物

7

反応物 4

HCID 8083MorpholineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxideHCID 597592542-[(4-{2-[(4-Bromobenzyl)(5-ethylpyrimidin-2-yl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester

生成物 1

HCID 597589862-[(4-{2-[(5-Ethylpyrimidin-2-yl)(4-morpholin-4-ylbenzyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester収率 49.5%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

tris(Dibenzylideneacetone)dipalladium (32 mg), 2-(di-tert-butylphosphino)biphenyl (21 mg) and sodium tert-butoxide (73 mg) were added to a 20 mL screw cap test tube substituted with nitrogen, and a solution of 2-[(4-{2-[(4-bromobenzyl)(5-ethylpyrimidin-2-yl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester (400 mg) synthesized in Example 402-1 and morpholine (91 mg) in toluene (1.4 mL) was added thereto. The test tube was capped, and stirred at 110° C. for 8 hr. After cooling to room temperature, the solution was directly purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=3:1 to 2:1) to give the title compound (200 mg) as a colorless oil.

後処理

  1. customcap test tube
  2. customThe test tube was capped
  3. temperatureAfter cooling to room temperature
  4. customthe solution was directly purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=3:1 to 2:1)

出典と根拠

ORDレコード
ord-4ad6bc93c9c34e318f2f4c7cd84f8df6
出典データセット
uspto-grants-2011_09
特許番号
US08026370B2

反応ノート

読み込み中…