Diisopropylethylamine → 2-[(6-Fluoro-4H-benzo[1,3]dioxine-8-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester

HRID 1047716

반응식

HRID 1047716 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:12]([OH:14])=O)[C:5]2[O:10][CH2:9][O:8][CH2:7][C:6]=2[CH:11]=1.[CH2:15]([O:17][C:18]([C:20]1([NH2:29])[CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21]1)=[O:19])[CH3:16].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>[CH2:15]([O:17][C:18]([C:20]1([NH:29][C:12]([C:4]2[C:5]3[O:10][CH2:9][O:8][CH2:7][C:6]=3[CH:11]=[C:2]([F:1])[CH:3]=2)=[O:14])[CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21]1)=[O:19])[CH3:16]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 27799016-fluoro-4H-1,3-benzodioxine-8-carboxylic acidHCID 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-carboxylate

생성물 1

HCID 593143692-[(6-Fluoro-4H-benzo[1,3]dioxine-8-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester수율 95.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 6-fluoro-4H-benzo[1,3]dioxine-8-carboxylic acid (386 mg, 1.95 mmol), 2-amino-indan-2-carboxylic acid ethyl ester (400 mg, 1.95 mmol), HATU (1.11 g, 2.93 mmol) in anhydrous DMF (8 mL) is added DIPEA (484 μL, 2.93 mmol). The resulting solution is stirred at RT overnight. After the removal of DMF in vacuo, the residue is dissolved in EtOAc (70 mL) and washed with water (1×10 mL) and brine (2×10 mL). The organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. The residue is purified by flash column chromatography (120 g silica gel, gradient elution: 5-50% EtOAc in heptane) to give a pure product (61) as white solid (720 mg, 6%).

후처리

  1. customAfter the removal of DMF in vacuo
  2. dissolutionthe residue is dissolved in EtOAc (70 mL)
  3. washwashed with water (1×10 mL) and brine (2×10 mL)
  4. dry with materialThe organic layer is dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by flash column chromatography (120 g silica gel, gradient elution: 5-50% EtOAc in heptane)

출처 및 근거

ORD 기록
ord-907077d88b874d6785d4f002d9a8ecda
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569535B2

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