Sodium hydride → HCID 71534334、化合物

HRID 1755430ノート

反応式

HRID 1755430 の反応式
Br[C:2]1[C:3]2[N:4]([CH:9]=[CH:10][N:11]=2)[N:5]=[C:6]([Cl:8])[CH:7]=1.[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([NH2:22])=[N:18][C:19]=1[O:20][CH3:21].[H-].[Na+]>CN(C=O)C>[Cl:8][C:6]1[CH:7]=[C:2]([NH:22][C:17]2[CH:16]=[CH:15][C:14]([O:13][CH3:12])=[C:19]([O:20][CH3:21])[N:18]=2)[C:3]2[N:4]([CH:9]=[CH:10][N:11]=2)[N:5]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 467391485,6-Dimethoxypyridin-2-amineHCID 468352698-Bromo-6-chloroimidazo(1,2-b)pyridazine

生成物 1

HCID 71534334HCID 71534334、化合物収率 91.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

A mixture of 8-bromo-6-chloroimidazo[1,2-b]pyridazine (2 g, 8.6 mmol) and 5,6-dimethoxypyridin-2-amine (1.39 g, 9.03 mmol) in DMF (72 ml) was cooled to 0° C. To the mixture was added sodium hydride (1.1 g, 27.5 mmol, 60% dispersion in mineral oil). The reaction was stirred for 10 min then warmed to room temperature. After 15 h the reaction was quenched with saturated sodium bicarbonate solution, and then diluted with water and EtOAc. An insoluble solid was filtered off. The filtrate was separated and the aqueous phase was washed with EtOAc. The combined organic extracts were concentrated in vacuo and the residue obtained was crystallized from methanol to give 6-chloro-N-(5,6-dimethoxypyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (2.4 g, 7.85 mmol, 91.2%) as light brown needles. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 8.26 (br. s., 1H) 7.95 (s, 1H) 7.81 (s, 1H) 7.55 (s, 1H) 7.15 (d, J=7.93 Hz, 1H) 6.58 (d, J=8.31 Hz, 1H) 4.12 (s, 3H) 3.89 (s, 3H); LC/MS: 305.9 [MH]+.

後処理

  1. temperaturethen warmed to room temperature
  2. customAfter 15 h the reaction was quenched with saturated sodium bicarbonate solution
  3. additiondiluted with water and EtOAc
  4. filtrationAn insoluble solid was filtered off
  5. customThe filtrate was separated
  6. washthe aqueous phase was washed with EtOAc
  7. concentrationThe combined organic extracts were concentrated in vacuo
  8. customthe residue obtained
  9. customwas crystallized from methanol

出典と根拠

ORDレコード
ord-6fd3233990ea48598cf851fcd2356294
出典データセット
uspto-grants-2015_10
特許番号
US09169259B2

反応ノート

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