Triethylamine → 3-Amino-6-bromo-N-pyridin-3-ylpyrazine-2-carboxamide

HRID 217782

反応式

HRID 217782 の反応式
[NH2:1][C:2]1[C:3]([C:9]([OH:11])=O)=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.[NH2:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>O.CN(C=O)C>[NH2:1][C:2]1[C:3]([C:9]([NH:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[O:11])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 100093-AminopyridineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 185216003-Amino-6-bromopyrazine-2-carboxylic acid2 回

生成物 1

HCID 104021623-Amino-6-bromo-N-pyridin-3-ylpyrazine-2-carboxamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
-2.5 °C

実験手順

3-Amino-6-bromopyrazine-2-carboxylic acid (1.07 kg), 3-aminopyridine (460 g), triethylamine (680 ml) and DMF (6.4 L) were charged into a reactor. The mixture was cooled to −5 to 0° C. and stirred for 15 min. Under a nitrogen flow, HATU (1.8 kg) was slowly added in many portions while maintaining the temperature below 10° C. Upon addition, thick yellow precipitate formed. After addition, the mixture was stirred at 20-25° C. for 1 h. The reaction was analysed for completion (3-Amino-6-bromopyrazine-2-carboxylic acid=0%). Water (13 L) was added under vigorous stirring. The yellow suspension was stirred at 25° C. for 30 min. The suspension was filtered and the filter cake was recharged into reactor. Water (13 L) was charged. The yellow suspension was warmed to 50° C. and stirred at this temperature for 2 h. The suspension was filtered and the filter cake was washed with water. The wet product (3-Amino-6-bromo-N-(pyridin-3-yl)pyrazine-2-carboxamide) was dried in oven at 55° C. under a flow of nitrogen. (1.14 Kg).

後処理

  1. temperaturewhile maintaining the temperature below 10° C
  2. additionUpon addition, thick yellow precipitate
  3. customformed
  4. additionAfter addition
  5. stirringthe mixture was stirred at 20-25° C. for 1 h
  6. stirringThe yellow suspension was stirred at 25° C. for 30 min
  7. filtrationThe suspension was filtered
  8. customthe filter cake was recharged into reactor
  9. additionWater (13 L) was charged
  10. temperatureThe yellow suspension was warmed to 50° C.
  11. stirringstirred at this temperature for 2 h
  12. filtrationThe suspension was filtered
  13. washthe filter cake was washed with water
  14. dry with materialThe wet product (3-Amino-6-bromo-N-(pyridin-3-yl)pyrazine-2-carboxamide) was dried in oven at 55° C. under a flow of nitrogen

出典と根拠

ORDレコード
ord-6384f54f3cb9492f82fd984df8d55947
出典データセット
uspto-grants-2012_06
特許番号
US08198285B2

関連ノート

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