Sodium hydride → HCID 71534334, 화합물

HRID 1755430노트

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HRID 1755430 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 71534334HCID 71534334, 화합물수율 91.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-6fd3233990ea48598cf851fcd2356294
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09169259B2

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