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Potassium Carbonate → 5-(2-Bromo-5-fluoro-pyridin-4-yl)-2,2-bis-fluoromethyl-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-ylamine

HRID 474110
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HRID 474110 반응식
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([NH:19]S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)([CH3:18])[CH2:9][O:10][C:11]([C:16]#[N:17])([CH2:14][F:15])[CH2:12][F:13])[C:5]([F:32])=[CH:4][N:3]=1.C(N[C@H](C(O)=O)CS)(=O)C.C([O-])([O-])=O.[K+].[K+]>CCO>[Br:1][C:2]1[CH:7]=[C:6]([C:8]2([CH3:18])[CH2:9][O:10][C:11]([CH2:14][F:15])([CH2:12][F:13])[C:16]([NH2:17])=[N:19]2)[C:5]([F:32])=[CH:4][N:3]=1
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참가 물질

5

반응물 3

HCID 11430Potassium Carbonate2회HCID 12035N-Acetyl-L-Cysteine2회HCID 86668082N-[1-(2-bromo-5-fluoro-pyridin-4-yl)-2-(cyano-bis-fluoromethyl-methoxy)-1-methyl-ethyl]-2-nitro-benzenesulfonamide

생성물 1

HCID 866680815-(2-Bromo-5-fluoro-pyridin-4-yl)-2,2-bis-fluoromethyl-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-ylamine

시약·촉매·용매 1

HCID 702
Ethanol
용매

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온도
85 °C

실험 절차

A solution of N-[1-(2-bromo-5-fluoro-pyridin-4-yl)-2-(cyano-bis-fluoromethyl-methoxy)-1-methyl-ethyl]-2-nitro-benzenesulfonamide (840 mg, 1.563 mmol), N-acetyl-L-cysteine (510 mg, 3.13 mmol) and K2CO3 (432 mg, 3.130 mmol) in abs. EtOH (10 ml) was stirred at 85° C. for 18 h. N-acetyl-L-cysteine (250 mg, 1.533 mmol) and K2CO3 (210 mg, 1.519 mmol) was added and stirring at 85° C. was continued for 18 h. The reaction mixture was concentrated to ⅓ of its volume, quenched with 10% aq. K2CO3 soln. and 3× extracted with TBME. The combined org. phases were washed with sat. aq. NaHCO3 soln, brine, dried over Na2SO4, filtered and concentrated to leave the crude title compound that was purified by NP-HPLC (Alltech Grom Saphir65 Si 10 μm column, 150×30 mm, gradient n-heptane:EtOAc:MeOH 68:30:2 to 0:65:35),

후처리

  1. concentrationThe reaction mixture was concentrated
  2. customquenched with 10% aq. K2CO3 soln
  3. extractionand 3× extracted with TBME
  4. washphases were washed with sat. aq. NaHCO3 soln
  5. dry with materialbrine, dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-89b7c9cc4cf74be7bdceda0fbaba3543
출처 데이터셋
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08637508B2

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