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

HRID 1047896노트

반응식

HRID 1047896 반응식
[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-4d9b20dc85db436e92f258bb34e08a92
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569535B2

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