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Triethylamine → 7-(7-hydroxy-6-methoxyquinolin-4-yloxy)-N-(5-methylisoxazol-3-yl)-2,3-dihydrobenzo[b][1,4]oxazine-4-carboxamide

HRID 1712975
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HRID 1712975 반응식
[O:1]1[CH2:6][CH2:5][NH:4][C:3]2[CH:7]=[CH:8][C:9]([O:11][C:12]3[C:21]4[C:16](=[CH:17][C:18]([OH:24])=[C:19]([O:22][CH3:23])[CH:20]=4)[N:15]=[CH:14][CH:13]=3)=[CH:10][C:2]1=2.[CH3:25][C:26]1[O:30][N:29]=[C:28]([NH:31][C:32](=O)[O:33]C2C=CC([N+]([O-])=O)=CC=2)[CH:27]=1.C(N(CC)CC)C>C1COCC1>[OH:24][C:18]1[CH:17]=[C:16]2[C:21]([C:12]([O:11][C:9]3[CH:8]=[CH:7][C:3]4[N:4]([C:32]([NH:31][C:28]5[CH:27]=[C:26]([CH3:25])[O:30][N:29]=5)=[O:33])[CH2:5][CH2:6][O:1][C:2]=4[CH:10]=3)=[CH:13][CH:14]=[N:15]2)=[CH:20][C:19]=1[O:22][CH3:23]
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 594634404-Nitrophenyl 5-methylisoxazol-3-ylcarbamateHCID 1359667514-(3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yloxy)-6-methoxyquinolin-7-ol

생성물 1

HCID 1359226927-(7-hydroxy-6-methoxyquinolin-4-yloxy)-N-(5-methylisoxazol-3-yl)-2,3-dihydrobenzo[b][1,4]oxazine-4-carboxamide수율 15.3%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
50 °C

실험 절차

A 25-mL round bottomed flask was charged with 4-(3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yloxy)-6-methoxyquinolin-7-ol (0.124 g, 0.38 mmol), 4-nitrophenyl 5-methylisoxazol-3-ylcarbamate (0.11 g, 0.40 mmol), and THF (5.0 mL). Triethylamine (0.160 mL, 1.1 mmol) was added, the system was purged with argon, and the tube was sealed. The mixture stirred at 50° C. for 16 h. The reaction mixture was concentrated and the residue was purified via column chromatography on silica gel (RediSep 40 g column, 100% ethyl acetate for 10 min, followed by 5% methanol/dichloromethane for 20 min) to afford 7-(7-hydroxy-6-methoxyquinolin-4-yloxy)-N-(5-methylisoxazol-3-yl)-2,3-dihydrobenzo[b][1,4]oxazine-4-carboxamide (0.026 g, 15% yield) as a yellow solid.

후처리

  1. customthe system was purged with argon
  2. customthe tube was sealed
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue was purified via column chromatography on silica gel (RediSep 40 g column, 100% ethyl acetate for 10 min, followed by 5% methanol/dichloromethane for 20 min)

출처 및 근거

ORD 기록
ord-dd37c393ebdb4c2d8ce12eff83be3ef3
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07795254B2

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