Imidazole → HCID 178423529、化合物

HRID 571385ノート

反応式

HRID 571385 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[C:12]3[CH:13]=[N:14][C:15]([NH2:17])=[CH:16][C:11]=3[N:10](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:9]=2)[CH:5]=[CH:4][N:3]=1.N1C=CN=C1.C1N=CN([C:47]([N:49]2C=N[CH:51]=[CH:50]2)=[O:48])C=1.NCC1[CH:61]=[CH:60][N:59]=[CH:58][CH:57]=1.C([SiH](CC)CC)C.[C:69]([OH:75])([C:71]([F:74])([F:73])[F:72])=[O:70]>C(Cl)Cl>[F:72][C:71]([F:74])([F:73])[C:69]([O-:75])=[O:70].[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[C:12]3[CH:13]=[N:14][C:15]([NH:17][C:47](=[O:48])[NH:49][CH2:50][C:51]4[CH:61]=[CH:60][N:59]=[CH:58][CH:57]=4)=[CH:16][C:11]=3[NH:10][N:9]=2)[CH:5]=[CH:4][NH+:3]=1

参加物

8

反応物 6

HCID 795ImidazoleHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 682631,1'-CarbonyldiimidazoleHCID 773174-PyridinemethanamineHCID 895258183-(2-methylpyridin-4-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-amine2 回

生成物 1

HCID 178423529HCID 178423529、化合物収率 36.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

A suspension of 3-(2-methylpyridin-4-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-amine (intermediate 5a; 33.4 mg, 0.071 mmol) and imidazole (14.59 mg, 0.214 mmol) in DCM (0.5 mL) was added to a solution of CDI (69.5 mg, 0.429 mmol) in DCM (0.5 mL) and the mixture was stirred at RT. After 3 h, 4-(aminomethyl)pyridine (0.062 mL, 0.571 mmol) was added and the mixture was left at the same temperature for additional 30 min. Volatiles were removed in vacuo and the residue was purified by chromatography on silica gel over a gradient of 0-50% (20% MeOH in EtOAc) in DCM to yield a solid, which was directly dissolved in DCM (1 mL), treated with triethylsilane (0.011 mL, 0.071 mmol) and TFA (0.1 mL, 1.298 mmol). After overnight stirring at RT the volatiles were concentrated in vacuo. The residue was purified via reverse phase HPLC over a gradient of 5-20% MeCN in H2O with 0.1% TFA to yield 2-methyl-4-(6-{[(pyridin-4-ylmethyl)carbamoyl]amino}-1H-pyrazolo[4,3-c]pyridin-3-yl)pyridinium trifluoroacetate (9 mg, 0.026 mmol, 36%) as a solid. MS ESI calc'd. for C19H18N7O [M+1]+ 360, found 360.

後処理

  1. waitthe mixture was left at the same temperature for additional 30 min
  2. customVolatiles were removed in vacuo
  3. customthe residue was purified by chromatography on silica gel over a gradient of 0-50% (20% MeOH in EtOAc) in DCM
  4. customto yield a solid, which
  5. stirringAfter overnight stirring at RT the volatiles
  6. concentrationwere concentrated in vacuo
  7. customThe residue was purified via reverse phase HPLC over a gradient of 5-20% MeCN in H2O with 0.1% TFA

出典と根拠

ORDレコード
ord-591970f285ee41f193edd75635fa9147
出典データセット
uspto-grants-2015_05
特許番号
US09023865B2

反応ノート

読み込み中…