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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
ノート
印刷プレビュー

反応式

HRID 474110 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11430Potassium Carbonate2 回HCID 12035N-Acetyl-L-Cysteine2 回HCID 86668082N-[1-(2-bromo-5-fluoro-pyridin-4-yl)-2-(cyano-bis-fluoromethyl-methoxy)-1-methyl-ethyl]-2-nitro-benzenesulfonamide

生成物 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

試薬・触媒・溶媒 1

HCID 702
Ethanol
溶媒

反応条件

温度
85 °C

実験手順

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),

後処理

  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

出典と根拠

ORDレコード
ord-89b7c9cc4cf74be7bdceda0fbaba3543
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08637508B2

反応ノート

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