Acetic Acid → 4-chloro-N-(6-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-yl)picolinamide

HRID 389625ノート

反応式

HRID 389625 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([NH:19][NH2:20])=O)[N:12]=2)=[O:9])[CH:3]=1.C[N:22]([CH3:26])[C:23](=O)[CH3:24].[CH:27]1(N)CC1.C(O)(=O)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]3[N:22]([CH:23]4[CH2:27][CH2:24]4)[CH:26]=[N:20][N:19]=3)[N:12]=2)=[O:9])[CH:3]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 31374DimethylacetamideHCID 69828CyclopropylamineHCID 581030194-chloro-N-(6-(hydrazinecarbonyl)pyridin-2-yl)picolinamide

生成物 1

HCID 581030634-chloro-N-(6-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-yl)picolinamide収率 72%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
150 °C

実験手順

To a suspension of 4-chloro-N-(6-(hydrazinecarbonyl)pyridin-2-yl)picolinamide (1.00 g, 3.43 mmol) in toluene (0.20 M) was added a mixture of N,N-dimethylforinamide.N,N-dimethylacetamide (1.14 mL, 8.56 mmol), cyclopropylamine (873 μL, 13.7 mmol), and acetic acid (194 μL, 3.43 mmol). The reaction mixture was heated to 150° C. for 30 minutes in a microwave reactor. The reaction product was concentrated under reduced pressure, and the residue was suspended in acetonitrile/diethyl ether (15 mL, 1:1 ratio), filtered, and the solid washed with acetonitrile/diethylether (2×10 mL). The filtrate was concentrated and the solid thus obtained was purified as above. The combined solids were dried under reduced pressure to afford 842 mg (72% yield) of 4-chloro-N-(6-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-yl)picolinamide as a white solid.

後処理

  1. additionwas added
  2. additiona mixture of N,N-dimethylforinamide
  3. concentrationThe reaction product was concentrated under reduced pressure
  4. filtrationfiltered
  5. washthe solid washed with acetonitrile/diethylether (2×10 mL)
  6. concentrationThe filtrate was concentrated
  7. customthe solid thus obtained
  8. customwas purified as above
  9. customThe combined solids were dried under reduced pressure

出典と根拠

ORDレコード
ord-5bd5d642302c492eac315058297f7ce0
出典データセット
uspto-grants-2013_02
特許番号
US08378108B2

反応ノート

読み込み中…