Benzoic Acid → HCID 44199933、化合物

HRID 2061164ノート

反応式

HRID 2061164 の反応式
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[O-]S([O-])(=O)=O.[Na+].[Na+].[CH3:50][N:51]1[C:60]2[C:55](=[CH:56][N:57]=[C:58]([CH3:61])[CH:59]=2)[CH:54]=[C:53]([C:62]2[CH:63]=[C:64]([NH:69]/[C:70](/[NH2:73])=[N:71]/O)[CH:65]=[CH:66][C:67]=2[CH3:68])[C:52]1=[O:74]>CN(C=O)C>[CH3:50][N:51]1[C:60]2[C:55](=[CH:56][N:57]=[C:58]([CH3:61])[CH:59]=2)[CH:54]=[C:53]([C:62]2[CH:63]=[C:64]([NH:69][C:70]3[N:71]=[C:1]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[O:9][N:73]=3)[CH:65]=[CH:66][C:67]=2[CH3:68])[C:52]1=[O:74]

参加物

7

反応物 5

HCID 243Benzoic AcidHCID 24436Sodium SulfateHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178422078HCID 178422078、化合物

生成物 1

HCID 44199933HCID 44199933、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a solution of benzoic acid (0.67 g, 5.5 mmol), HATU (2.09 g, 11 mmol) and DIPEA (1.05 mL, 6 mmol) in dry DMF (10 mL) at rt in the presence of anhydrous Na2SO4 (7 g, 50 mmol) was added 17 (1.69 g, 5 mmol) slowly. The consumption of 17 was determined to be completed by LC/MS. Additional anhydrous DMF (40 mL) was added and the mixture was heated at 100° C. for 1 h. Solid was filtered off and most of DMF was removed under vacuum. The residue was partitioned between a mixture of water (150 mL), aqueous Na2CO3 (2 M, 10 mL), EtOAc (200 mL) and MeOH (20 mL). The organic phase was washed further with water (2×50 mL). After drying and removal of EtOAc, the solid residue was suspended and stirred in ACN (40 mL) for 16 h. Filtration and washing with copies amounts of ACN yielded A7 as a solid. 1H NMR (400 MHz, d4-MeOH) δ 9.03 (s, 1H), 8.12 (s, 1H), 8.1 (d, J=1.5 Hz, 1H), 8.05 (s, 1H), 7.83 (s, 1H), 7.65 (d, J=6.2 Hz, 1H), 7.59 (d, J=6.3 Hz, 1H), 7.57 (d, J=7.2 Hz, 1H), 7.5 (d, J=2.4 Hz, 1H), 7.43 (dd, J=8.3, 2.5 Hz, 1H), 7.27 (d, J=8.4 Hz, 1H), 3.84 (s, 3H), 2.83 (s, 3H), 2.18 (s, 3H). MS m/z 424.1 (M+1).

後処理

  1. customThe consumption of 17
  2. additionAdditional anhydrous DMF (40 mL) was added
  3. filtrationSolid was filtered off and most of DMF
  4. customwas removed under vacuum
  5. customThe residue was partitioned between a mixture of water (150 mL), aqueous Na2CO3 (2 M, 10 mL), EtOAc (200 mL) and MeOH (20 mL)
  6. washThe organic phase was washed further with water (2×50 mL)
  7. customAfter drying
  8. customremoval of EtOAc
  9. filtrationFiltration
  10. washwashing with copies amounts of ACN

出典と根拠

ORDレコード
ord-2b0bdf986410460ea64649740135af3d
出典データセット
uspto-grants-2012_10
特許番号
US08278452B2

反応ノート

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