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5-Chloropyrazinoic acid → (R)-N-(3-(2-Amino-5,5-difluoro-4-methyl-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-chloropyrazine-2-carboxamide

HRID 1520242
ノート
印刷プレビュー

反応式

HRID 1520242 の反応式
[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.[NH2:30][C:31]1[CH:32]=[CH:33][C:34]([F:47])=[C:35]([C@:37]2([CH3:46])[C:42]([F:44])([F:43])[CH2:41][O:40][C:39]([NH2:45])=[N:38]2)[CH:36]=1.C([O-])(O)=O.[Na+]>CO>[NH2:45][C:39]1[O:40][CH2:41][C:42]([F:43])([F:44])[C@:37]([C:35]2[CH:36]=[C:31]([NH:30][C:8]([C:5]3[CH:4]=[N:3][C:2]([Cl:1])=[CH:7][N:6]=3)=[O:10])[CH:32]=[CH:33][C:34]=2[F:47])([CH3:46])[N:38]=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

6

反応物 4

HCID 4654725-Chloropyrazinoic acidHCID 516892Sodium BicarbonateHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 58304207(R)-4-(5-amino-2-fluoro-phenyl)-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamine2 回

生成物 1

HCID 53240912(R)-N-(3-(2-Amino-5,5-difluoro-4-methyl-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-chloropyrazine-2-carboxamide

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
0 °C

実験手順

5-Chloropyrazine-2-carboxylic acid (367 mg, 2.31 mmol) was combined with MeOH (25 ml) to give a colorless solution. 4-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (DMTMM, 705 mg, 2.55 mmol) was added at 0° C. and the solution was stirred at 0° C. for 30 min. A solution of (R)-4-(5-amino-2-fluoro-phenyl)-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-ylamine (intermediate A 8.1, 600 mg, 2.31 mmol) in MeOH (10 ml) was added dropwise and the reaction mixture was stirred overnight at 0° C. Sat. aq. NaHCO3 was added and the product was extracted with three portions of AcOEt. The combined organic layers were dried over Na2SO4 and concentrated under vacuum. The crude material was purified by flash chromatography (SiO2, 50 g, 50 to 100% EtOAc in heptane). White solid (540 mg, 58%). MS (ISP): m/z=400.1 [M+H]+.

後処理

  1. customto give a colorless solution
  2. stirringthe reaction mixture was stirred overnight at 0° C
  3. extractionthe product was extracted with three portions of AcOEt
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customThe crude material was purified by flash chromatography (SiO2, 50 g, 50 to 100% EtOAc in heptane)

出典と根拠

ORDレコード
ord-c0bfb9703343427291d655376635bf02
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09073909B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート