Diisopropylethylamine → 2-(2-Cyclobutoxy-5-hydroxymethyl-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

HRID 1047896ノート

反応式

HRID 1047896 の反応式
[CH:1]1([O:5][C:6]2[C:14]([CH3:15])=[CH:13][C:12]([CH2:16][OH:17])=[CH:11][C:7]=2[C:8]([OH:10])=O)[CH2:4][CH2:3][CH2:2]1.[CH2:18]([O:20][C:21]([C:23]1([NH2:32])[CH2:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24]1)=[O:22])[CH3:19].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>CN(C=O)C.O>[CH2:18]([O:20][C:21]([C:23]1([NH:32][C:8](=[O:10])[C:7]2[CH:11]=[C:12]([CH2:16][OH:17])[CH:13]=[C:14]([CH3:15])[C:6]=2[O:5][CH:1]2[CH2:2][CH2:3][CH2:4]2)[CH2:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24]1)=[O:22])[CH3:19]

参加物

7

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 593143012-Cyclobutoxy-5-hydroxymethyl-3-methyl-benzoic acid

生成物 1

HCID 593141022-(2-Cyclobutoxy-5-hydroxymethyl-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester収率 10%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2-cyclobutoxy-5-hydroxymethyl-3-methyl-benzoic acid (410 mg, 1.7 mmol), 2-amino-indan-2-carboxylic acid ethyl ester (425 mg, 1.7 mmol), HATU (760 mg, 2 mmol) in anhydrous DMF (5 mL) is added DIPEA (4354, 2.5 mmol). The resulting solution is stirred at RT overnight. Water (10 mL) is poured into the reaction mixture, and then extracted with EtOAc (3×7 mL). The combined organic layers are concentrated in vacuo. The residue is purified by reverse phase chromatography (gradient elution: 20-100% ACN in water) to give product (285) as colorless oil (70 mg, 10%).

後処理

  1. extractionextracted with EtOAc (3×7 mL)
  2. concentrationThe combined organic layers are concentrated in vacuo
  3. customThe residue is purified by reverse phase chromatography (gradient elution: 20-100% ACN in water)

出典と根拠

ORDレコード
ord-4d9b20dc85db436e92f258bb34e08a92
出典データセット
uspto-grants-2013_10
特許番号
US08569535B2

反応ノート

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