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Diisopropylethylamine → 5-Cyano-2-[(5,6,7,8-tetrahydro-naphthalene-1-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester

HRID 1047756
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HRID 1047756 반응식
[C:1]1([C:11]([OH:13])=O)[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:14]([O:16][C:17]([C:19]1([NH2:30])[CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:28]#[N:29])[CH:25]=2)[CH2:20]1)=[O:18])[CH3:15].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>[CH2:14]([O:16][C:17]([C:19]1([NH:30][C:11]([C:1]2[C:10]3[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=3[CH:4]=[CH:3][CH:2]=2)=[O:13])[CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:28]#[N:29])[CH:25]=2)[CH2:20]1)=[O:18])[CH3:15]
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참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 2396045,6,7,8-Tetrahydro-1-naphthalenecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 593141522-Amino-5-cyano-indan-2-carboxylic acid ethyl ester

생성물 1

HCID 593141255-Cyano-2-[(5,6,7,8-tetrahydro-naphthalene-1-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester
수율 70%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 5,6,7,8-tetrahydro-naphthalene-1-carboxylic acid (306 mg, 1.74 mmol), 2-amino-5-cyano-indan-2-carboxylic acid ethyl ester (601 mg, 2.61 mmol), HATU (992 mg, 2.61 mmol) in anhydrous DMF (15 mL) is added DIPEA (431 μL, 2.61 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%-80% EtOAc in heptane) to give a pure product (106) as white solid (473 mg, 70%).

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%-80% EtOAc in heptane)

출처 및 근거

ORD 기록
ord-8f83365e62074dd38e828da2911ced35
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08569535B2

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