Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → methyl 3-phenyl-1-(5-sulfamoylnicotinamido)-1H-pyrrole-2-carboxylate

HRID 2170138ノート

反応式

HRID 2170138 の反応式
[NH2:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:3]1[C:13]([O:15][CH3:16])=[O:14].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[S:41]([C:45]1[CH:46]=[N:47][CH:48]=[C:49]([CH:53]=1)[C:50](O)=[O:51])(=[O:44])(=[O:43])[NH2:42]>CN(C=O)C.CN(C1C=CN=CC=1)C>[C:7]1([C:4]2[CH:5]=[CH:6][N:2]([NH:1][C:50](=[O:51])[C:49]3[CH:53]=[C:45]([S:41](=[O:43])(=[O:44])[NH2:42])[CH:46]=[N:47][CH:48]=3)[C:3]=2[C:13]([O:15][CH3:16])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

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 534853495-Sulfamoylpyridine-3-carboxylic acidHCID 90386150HCID 90386150、化合物

生成物 1

HCID 90386125methyl 3-phenyl-1-(5-sulfamoylnicotinamido)-1H-pyrrole-2-carboxylate収率 32.4%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒2 回

実験手順

To a stirred solution of methyl 1-amino-3-phenyl-1H-pyrrole-2-carboxylate (2.00 g, 9.25 mmol) in DMF (20 mL) was added DMAP (3.39 g, 27.7 mmol) and HATU (10.6 g, 27.7 mmol). The reaction mixture was stirred for 15 minutes and a solution of 5-sulfamoylnicotinic acid (3.74 g, 18.5 mmol) dissolved in DMF was added. The reaction mixture was stirred at room temperature for 14 h. The reaction mixture was concentrated under reduced pressure to remove DMF and saturated solution of citric acid was added to the residue until the pH was 3. The solution was extracted with CH2Cl2 and the organic layer was separated, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using CombiFlash (REDISEP®, neutral alumina, 40 g, 13% methanol in CH2Cl2) to afford methyl 3-phenyl-1-(5-sulfamoylnicotinamido)-1H-pyrrole-2-carboxylate (1.20 g, 32.4%). LCMS Condition B-39: retention time 1.79 min, [M−1]=399.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.54 (s, 3H), 6.34 (d, J=3.2 Hz, 1H), 7.32-7.44 (m, 7H), 7.80 (br s, 2H), 8.68 (t, J=2.0 Hz, 1H), 9.20 (d, J=2.0 Hz, 1H), 9.30 (d, J=2.0 Hz, 1H).

後処理

  1. additionwas added
  2. stirringThe reaction mixture was stirred at room temperature for 14 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customto remove DMF and saturated solution of citric acid
  5. additionwas added to the residue until the pH was 3
  6. extractionThe solution was extracted with CH2Cl2
  7. customthe organic layer was separated
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-c2dcebf59e65442ab78d75c43f1213b3
出典データセット
uspto-grants-2015_06
特許番号
US09050345B2

反応ノート

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