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Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 11963219、化合物

HRID 2359667
ノート
印刷プレビュー

反応式

HRID 2359667 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][C:17]=1[F:23].[CH3:24][N:25]1[C:29]([C:30]2[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=2)=[C:28]([C:36](O)=[O:37])[C:27](=[O:39])[N:26]1[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:36]([C:28]2[C:27](=[O:39])[N:26]([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[N:25]([CH3:24])[C:29]=2[C:30]2[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=2)=[O:37])=[CH:18][C:17]=1[F:23]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 114269974-((6,7-Dimethoxyquinolin-4-yl)oxy)-3-fluorobenzenamineHCID 59598434HCID 59598434、化合物

生成物 1

HCID 11963219HCID 11963219、化合物収率 22%

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
HCID 6344Dichloromethane溶媒

実験手順

4-(6,7-dimethoxyquinolin-4-yloxy)-3-fluorobenzenamine (628.9 mg, 2.001 mmol) and 1-methyl-3-oxo-2-phenyl-5-(pyridin-4-yl)-2,3-dihydro-1H-pyrazole-4-carboxylic acid (520 mg, 1.76 mmol) (1.679 g of a ˜30% by weight solution of acid in DMF) was dissolved in DCM (20 ml) and HATU (1.042 g, 2.740 mmol) was added. The reaction was stirred under nitrogen at room temperature overnight, and then filtered. The filtered solid was washed with dichloromethane, and the filtrate was concentrated and purified on silica gel (DCM→50:1→25:1→10:1 DCM/MeOH). The fractions with product were collected, concentrated, and purified on silica gel (30:1→20:1→10:1 DCM/MeOH). Fractions with product collected, concentrated, and purified again on silica gel (25:1→20:1 DCM/MeOH). Fractions with pure product collected and concentrated to give desired N-(4-(6,7-dimethoxyquinolin-4-yloxy)-3-fluorophenyl)-1-methyl-3-oxo-2-phenyl-5-(pyridin-4-yl)-2,3-dihydro-1H-pyrazole-4-carboxamide (225.9 mg, 0.382 mmol, 22% yield). MS (ESI pos. ion) m/z: 592 (MH+). Calc'd exact mass for C33H26FN5O5: 591. 1H NMR (400 MHz, CDCl3): 10.96 (s, 1H), 8.88 (d, J=4.0 Hz, 2H), 8.48 (d, J=6.0 Hz, 1H), 7.83 (d, J=12 Hz, 1H), 7.65-7.47 (m, 8H), 7.41 (s, 1H), 7.30 (d, J=10.0 Hz, 1H), 7.16 (t, J=8.0 Hz, 1H), 6.40 (d, J=5.2 Hz, 1H), 4.05 (s, 6H), 3.20 (s, 3H).

後処理

  1. filtrationfiltered
  2. washThe filtered solid was washed with dichloromethane
  3. concentrationthe filtrate was concentrated
  4. custompurified on silica gel (DCM→50:1→25:1→10:1 DCM/MeOH)
  5. customThe fractions with product were collected
  6. concentrationconcentrated
  7. custompurified on silica gel (30:1→20:1→10:1 DCM/MeOH)
  8. customFractions with product collected
  9. concentrationconcentrated
  10. custompurified again on silica gel (25:1→20:1 DCM/MeOH)
  11. customFractions with pure product collected
  12. concentrationconcentrated

出典と根拠

ORDレコード
ord-8613ef4f9e874741906da2564134bdc4
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08685983B2

反応ノート

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