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Triethylamine → 4-bromo-N-[(3R,4S)-3-hydroxytetrahydro-2H-pyran-4-yl]quinoline-2-carboxamide

HRID 1497332
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HRID 1497332 반응식
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([OH:14])=O)[CH:3]=1.Cl.[NH2:16][C@H:17]1[CH2:22][CH2:21][O:20][CH2:19][C@@H:18]1[OH:23].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([NH:16][C@H:17]2[CH2:22][CH2:21][O:20][CH2:19][C@@H:18]2[OH:23])=[O:14])[CH:3]=1
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참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 155308124-Bromoquinoline-2-carboxylic acidHCID 67324376(3R,4S)-4-aminooxan-3-ol hydrochloride

생성물 1

HCID 602099134-bromo-N-[(3R,4S)-3-hydroxytetrahydro-2H-pyran-4-yl]quinoline-2-carboxamide

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
2회

실험 절차

To a solution of 4-bromoquinoline-2-carboxylic acid (A3) (0.5 g, 2.0 mmol) in 10 mL CH2Cl2 was added (3R,4S)-4-aminotetrahydro-2H-pyran-3-ol hydrogen chloride (0.37 g, 2.4 mmol), BOP reagent (1.1 g, 2.6 mmol), and triethylamine (0.83 mL, 6.0 mmol). The reaction was stirred at room temperature for 4.5 h, diluted with CH2Cl2, washed twice with water, dried over sodium sulfate, filtered, and concentrated. The resultant residue was subjected to silica gel chromatography eluting with 30-100% ethyl acetate in hexanes to afford 4-bromo-N-[(3R,4S)-3-hydroxytetrahydro-2H-pyran-4-yl]quinoline-2-carboxamide (O1) that gave a mass ion (ES+) of 353.2 (81Br) for M+H+.

후처리

  1. washwashed twice with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washeluting with 30-100% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-d73b1c9232d7494ab2df766c03317aea
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09199939B2

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