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N-methyl-2-pyrrolidone → N-[4-(1-{1-(4-Chlorophenyl)-2-[5-(2-methoxypyridin-3-yl)-1,3-dihydro-2H-isoindol-2-yl]-2-oxoethyl}butyl)benzoyl]-beta-alanine

HRID 2190892
ノート
印刷プレビュー

反応式

HRID 2190892 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:12]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([NH:24][CH2:25][CH2:26][C:27]([O:29]CC)=[O:28])=[O:23])=[CH:18][CH:17]=2)[CH2:13][CH2:14][CH3:15])[C:9](O)=[O:10])=[CH:4][CH:3]=1.CN(C(ON1N=N[C:42]2[CH:43]=[CH:44][CH:45]=[N:46][C:41]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Br[C:66]1[CH:67]=[C:68]2[C:72](=[CH:73][CH:74]=1)[CH2:71][NH:70][CH2:69]2.CN1[C:80](=[O:81])CCC1>CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH:12]([C:16]2[CH:17]=[CH:18][C:19]([C:22]([NH:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[O:23])=[CH:20][CH:21]=2)[CH2:13][CH2:14][CH3:15])[C:9]([N:70]2[CH2:71][C:72]3[C:68](=[CH:67][CH:66]=[C:74]([C:42]4[C:41]([O:81][CH3:80])=[N:46][CH:45]=[CH:44][CH:43]=4)[CH:73]=3)[CH2:69]2)=[O:10])=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 147958715-BromoisoindolineHCID 585538202-(4-Chlorophenyl)-3-(4-{[(3-ethoxy-3-oxopropyl)amino]carbonyl}phenyl)hexanoic acid

生成物 1

HCID 46870236
N-[4-(1-{1-(4-Chlorophenyl)-2-[5-(2-methoxypyridin-3-yl)-1,3-dihydro-2H-isoindol-2-yl]-2-oxoethyl}butyl)benzoyl]-beta-alanine

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of a single stereoisomer (of the four possible) of 2-(4-chlorophenyl)-3-(4-{[(3-ethoxy-3-oxopropyl)amino]carbonyl}phenyl)hexanoic acid (EXAMPLE 1, Step C, 142 mg, 0.318 mmol) in NMP (3 mL) at room temperature was added HATU (133 mg, 0.350 mmol) and DIPEA (222 μl, 1.27 mmol). After one hour, 5-bromoisoindoline (94 mg, 0.48 mmol) was added, then the mixture was stirred at rt until the reaction was complete by LC-MS analysis. The mixture was then diluted with EtOAc then washed with water then saturated NaCl (aq). The organic layer was then dried over Na2SO4, filtered, then concentrated. The resulting residue was purified by silica gel chromatography eluting with 0-100% EtOAc/hexanes to provide the title compound as a white solid. LC2 1.53 min. (M+H)+ 627.

後処理

  1. washthen washed with water
  2. dry with materialThe organic layer was then dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue was purified by silica gel chromatography
  6. washeluting with 0-100% EtOAc/hexanes

出典と根拠

ORDレコード
ord-7fec6bb96cfd48bcb8c265596c12114b
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08324384B2

反応ノート

読み込み中…

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