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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
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HRID 1520242 반응식
[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
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6

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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-ylamine2회

생성물 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

시약·촉매·용매 1

HCID 887Methanol용매2회

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온도
0 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-c0bfb9703343427291d655376635bf02
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09073909B2

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