3-Aminopyridine → 4-Methyl-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-7-carboxylic acid pyridin-3-ylamide

HRID 1710451ノート

反応式

HRID 1710451 の反応式
[CH3:1][CH:2]1[N:7]2[C:8]3[CH:9]=[C:10]([C:15]([OH:17])=O)[CH:11]=[CH:12][C:13]=3[CH:14]=[C:6]2[C:5](=[O:18])[NH:4][CH2:3]1.CN(C(ON1N=[N:34][C:29]2[CH:30]=[CH:31][CH:32]=[N:33][C:28]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=NC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.NC1C=NC=CC=1>CN(C=O)C>[N:33]1[CH:32]=[CH:31][CH:30]=[C:29]([NH:34][C:15]([C:10]2[CH:11]=[CH:12][C:13]3[CH:14]=[C:6]4[C:5](=[O:18])[NH:4][CH2:3][CH:2]([CH3:1])[N:7]4[C:8]=3[CH:9]=2)=[O:17])[CH:28]=1

参加物

7

反応物 5

HCID 100093-AminopyridineHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 587675714-Methyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylic acid

生成物 1

HCID 119640054-Methyl-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-7-carboxylic acid pyridin-3-ylamide収率 89.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of 4-methyl-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-7-carboxylic acid (step f) (20 mg, 0.08 mmol) in 1 mL of DMF was added HATU (34.3 mg, 0.082 mmol), HOAt (6, 0.04 mmol) and diisopropylethylamine (29 uL, 0.164 mmol). After 15 min, 3-amino-pyridine in 1 mL of DMF was added. The mixture was stirred at room temperature for 48 h. The reaction was extracted with EtOAc several times, washed with water and brine. The combined organics were dried over MgSO4, filtered, and concentrated in vacuum. Purification by silica gel chromatography gave 23 mg of 4-methyl-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-7-carboxylic acid pyridin-3-ylamide 87% as a white solid. ESI-MS m/z 321.34 [M+H]+.

後処理

  1. extractionThe reaction was extracted with EtOAc several times
  2. washwashed with water and brine
  3. dry with materialThe combined organics were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. customPurification by silica gel chromatography

出典と根拠

ORDレコード
ord-56f2f932a08b4aff9ec481584207b2c7
出典データセット
uspto-grants-2010_09
特許番号
US07790712B2

反応ノート

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