Diisopropylamine → 2-methyl-5-nitro-N-(pyrimidin-5-yl)benzamide

HRID 2355095

반응식

HRID 2355095 반응식
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(NC(C)C)(C)C.[N:45]1[CH:50]=[C:49]([NH2:51])[CH:48]=[N:47][CH:46]=1>CN(C=O)C>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([NH:51][C:49]1[CH:50]=[N:45][CH:46]=[N:47][CH:48]=1)=[O:6]

참가 물질

6

반응물 4

HCID 7912DiisopropylamineHCID 344373Pyrimidin-5-amineHCID 5196832-Methyl-5-nitrobenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 248232552-methyl-5-nitro-N-(pyrimidin-5-yl)benzamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

In a 2 L round bottom flask with mechanical stirring was charged with 2-methyl-5-nitrobenzoic acid (20 g), HATU (38 g) and diisopropylamine (32 mL) in DMF (90 mL). This mixture was stirred for 30 min then pyrimidin-5-amine was added and the reaction was stirred for 18 hr. The LCMS showed complete conversion. DMF was removed under vacuum as much as possible then water was added and a solid precipitated out (use mechanical stirring). The tan solid was filtered and rinsed with water, then taken up in EtOAc, washed with brine, dried over MgSO4, filtered and concentrated down. The crude was taken up in EtOAc and the product 45 precipitated out. This was filtered and the filtrate was concentrated down and taken up in EtOAc/Hex. After standing overnight, more solids were filtered and were combined with the first crop. 2-methyl-5-nitro-N-(pyrimidin-5-yl)benzamide 45 was obtained as a light yellow solid.

후처리

  1. stirringThis mixture was stirred for 30 min
  2. stirringthe reaction was stirred for 18 hr
  3. customDMF was removed under vacuum as much as possible then water
  4. additionwas added
  5. customa solid precipitated out
  6. stirring(use mechanical stirring)
  7. filtrationThe tan solid was filtered
  8. washrinsed with water
  9. washwashed with brine
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated down
  13. customthe product 45 precipitated out
  14. filtrationThis was filtered
  15. concentrationthe filtrate was concentrated down
  16. filtrationmore solids were filtered

출처 및 근거

ORD 기록
ord-5d7b5c1d48794e1cb5ccdf93ebef697c
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07754717B2

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