Diisopropylethylamine → HCID 59314393、化合物

HRID 1047860ノート

反応式

HRID 1047860 の反応式
[CH2:1]([O:3][C:4]([C:6]1([NH2:15])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2].[CH2:16]([C:23]1[CH:31]=[C:30]([Br:32])[CH:29]=[CH:28][C:24]=1[C:25](O)=[O:26])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>>[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:25](=[O:26])[C:24]2[CH:28]=[CH:29][C:30]([Br:32])=[CH:31][C:23]=2[CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2]

参加物

5

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10921653Ethyl 2-amino-2,3-dihydro-1H-indene-2-carboxylateHCID 251406092-Benzyl-4-bromobenzoic acid

生成物 1

HCID 59314393HCID 59314393、化合物収率 86.2%

実験手順

2-Amino-indane-2-carboxylic acid ethyl ester (2) (250 mg, 1.2 mmol), 2-benzyl-4-bromo-benzoic acid (239) (354 mg, 1.2 mmol) and HATU (555 mg, 1.46 mmol) are taken in a vial, evacuated and refilled with nitrogen. Anhydrous DMF (2 mL) is added and stirring is initiated. After few min, DIPEA (0.302 mL, 1.82 mmol) is added and stirred at RT overnight. Analysis by tlc of the reaction mixture (silica, 50% EtOAc/heptanes) indicates complete consumption of the starting amine. Water (10 mL) is added, extracted with EtOAc (3×5 mL), dried over Na2SO4, concentrated and the crude product is chromatographed on a 25 g silica gel column using 20-50% EtOAc in heptane as a gradient to afford 2-(2-benzyl-4-bromo-benzoylamino)-indan-2-carboxylic acid ethyl ester (495 mg, 86%).

後処理

  1. customevacuated
  2. additionrefilled with nitrogen
  3. additionAnhydrous DMF (2 mL) is added
  4. stirringstirred at RT overnight
  5. customconsumption of the starting amine
  6. additionWater (10 mL) is added
  7. extractionextracted with EtOAc (3×5 mL)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customthe crude product is chromatographed on a 25 g silica gel column

出典と根拠

ORDレコード
ord-746aa8a9ec314f6da5881152f60e237c
出典データセット
uspto-grants-2013_10
特許番号
US08569535B2

反応ノート

読み込み中…