Triethylamine → 4-Bromoquinoline-2-carboxylic acid

HRID 1497324노트

반응식

HRID 1497324 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:13])[CH:3]=1.[NH2:15][C@@H:16]1[C@@H:21]([OH:22])[CH2:20][CH2:19][O:18][CH2:17]1.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]([OH:14])=[O:13])[CH:3]=1.[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:15][C@@H:16]2[C@@H:21]([OH:22])[CH2:20][CH2:19][O:18][CH2:17]2)=[O:14])[CH:3]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 155308124-Bromoquinoline-2-carboxylic acidHCID 55285677(3S,4S)-3-Aminotetrahydro-2H-pyran-4-OL

생성물 2

HCID 155308124-Bromoquinoline-2-carboxylic acidHCID 602099044-bromo-N-[(3S,4S)-4-hydroxytetrahydro-2H-pyran-3-yl]quinoline-2-carboxamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

4-Bromoquinoline-2-carboxylic acid (A3) was prepared as described in Example 1. To a solution of A3 (0.35 g, 1.4 mmol) in 6.0 mL CH2Cl2 was added (3S,4S)-3-aminotetrahydro-2H-pyran-4-ol (0.20 g, 1.7 mmol), BOP reagent (0.74 g, 1.7 mmol), and triethylamine (0.58 mL, 4.2 mmol). The reaction mixture was stirred at room temperature for 16 h, diluted with CH2Cl2, washed with water, dried over sodium sulfate, filtered, and concentrated. The resultant residue was subjected to silica gel chromatography eluting with 25-100% ethyl acetate in hexanes to afford 4-bromo-N-[(3S,4S)-4-hydroxytetrahydro-2H-pyran-3-yl]quinoline-2-carboxamide that gave a mass ion (ES+) of 353.1 (81Br) for M+H+.

후처리

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washeluting with 25-100% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-43e1082865624560852b0899dbf4a344
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199939B2

반응 노트

불러오는 중…