Diisopropylethylamine → 2-(2-Isobutyryl-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

HRID 1047848ノート

反応式

HRID 1047848 の反応式
[C:1]([C:6]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=O)(=[O:5])[CH:2]([CH3:4])[CH3:3].[CH2:16]([O:18][C:19]([C:21]1([NH2:30])[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22]1)=[O:20])[CH3:17].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>[CH2:16]([O:18][C:19]([C:21]1([NH:30][C:8](=[O:10])[C:7]2[CH:11]=[CH:12][CH:13]=[C:14]([CH3:15])[C:6]=2[C:1](=[O:5])[CH:2]([CH3:3])[CH3:4])[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22]1)=[O:20])[CH3:17]

参加物

6

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 593141812-Isobutyryl-3-methyl-benzoic acid

生成物 1

HCID 593142722-(2-Isobutyryl-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester収率 89.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2-isobutyryl-3-methyl-benzoic acid (227) (200 mg, 0.97 mmol), 2-amino-indan-2-carboxylic acid ethyl ester (220 mg, 1.07 mmol), HATU (441 mg, 1.16 mmol) in anhydrous DMF (10 mL) is added DIPEA (192 μL, 1.16 mmol). The resulting solution is stirred at RT overnight. After the removal of DMF in vacuo, the residue is dissolved in DCM (50 mL) and washed with water (1×5 mL) and brine (1×5 mL). The organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. The residue is purified by HPLC to give a pure product (228) as a pale yellow solid (340 mg, 89%).

後処理

  1. customAfter the removal of DMF in vacuo
  2. dissolutionthe residue is dissolved in DCM (50 mL)
  3. washwashed with water (1×5 mL) and brine (1×5 mL)
  4. dry with materialThe organic layer is dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by HPLC

出典と根拠

ORDレコード
ord-1845e479517e4873bf29498329093dfe
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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