Diisopropylethylamine → 2-(2-Cyclobutoxy-3-methyl-benzoylamino)-4,5-dichloro-indan-2-carboxylic acid ethyl ester

HRID 1047873노트

반응식

HRID 1047873 반응식
[CH:1]1([O:5][C:6]2[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:7]=2[C:8]([OH:10])=O)[CH2:4][CH2:3][CH2:2]1.[CH2:16]([O:18][C:19]([C:21]1([NH2:32])[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[C:26]([Cl:31])[C:27]=2[Cl:30])[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:32][C:8](=[O:10])[C:7]2[CH:11]=[CH:12][CH:13]=[C:14]([CH3:15])[C:6]=2[O:5][CH:1]2[CH2:2][CH2:3][CH2:4]2)[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[C:26]([Cl:31])[C:27]=2[Cl:30])[CH2:22]1)=[O:20])[CH3:17]

참가 물질

6

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 593141552-Cyclobutyloxy-3-methylbenzoic acidHCID 685903502-Amino-4,5-dichloro-indan-2-carboxylic acid ethyl ester

생성물 1

HCID 685899192-(2-Cyclobutoxy-3-methyl-benzoylamino)-4,5-dichloro-indan-2-carboxylic acid ethyl ester수율 76,529.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-cyclobutoxy-3-methyl-benzoic acid (225 mg, 1.1 mmol), 2-amino-4,5-dichloro-indan-2-carboxylic acid ethyl ester (254) (360 mg, 1.3 μmol), HATU 622 mg, 1.64 mmol) in anhydrous DMF (10 mL) is added DIPEA (360 μL, 2.20 mmol). The resulting solution is stirred at RT overnight. After the removal of DMF in vacuo, the residue is suspended in H2O (50 mL) and washed with EtOAc (3×50 mL). Organics are combined and washed successively with NaHCO3 and brine, and then the organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. The residue is purified by flash column chromatography (12 g silica gel, gradient elution: 0%-20% EtOAc in heptane) to give a pure product (255) as white powder (460 mg, 90%).

후처리

  1. customAfter the removal of DMF in vacuo
  2. washwashed with EtOAc (3×50 mL)
  3. washwashed successively with NaHCO3 and brine
  4. dry with materialthe organic layer is dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by flash column chromatography (12 g silica gel, gradient elution: 0%-20% EtOAc in heptane)

출처 및 근거

ORD 기록
ord-42ebbcaab35349438b723dac694c377c
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569535B2

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