Water → 6-((S)-sec-Butoxy)-7,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine

HRID 1524462

반응식

HRID 1524462 반응식
[H-].[Na+].Cl[C:4]1[C:5]([CH3:15])=[C:6]([CH3:14])[C:7]2[N:8]([C:10]([NH2:13])=[N:11][N:12]=2)[N:9]=1.[OH2:16]>C[C@H](O)CC.CN(C=O)C>[C@@H:5]([O:16][C:4]1[C:5]([CH3:15])=[C:6]([CH3:14])[C:7]2[N:8]([C:10]([NH2:13])=[N:11][N:12]=2)[N:9]=1)([CH2:6][CH3:7])[CH3:4]

참가 물질

6

반응물 3

HCID 962WaterHCID 24758Sodium hydrideHCID 580458046-Chloro-7,8-dimethyl-[1,2,4]triazolo[4,3-B]pyridazin-3-amine

생성물 1

HCID 580458716-((S)-sec-Butoxy)-7,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 444683(+)-2-Butanol용매2회

반응 조건

온도
0 °C

실험 절차

(S)-Butan-2-ol (1.7 ml) was initially charged at RT with stirring and cooled almost to 0° C. with an ice bath. Subsequently, the mixture was admixed with portions of sodium hydride (85 mg). The suspension formed was heated to 55° C. for 1.5 h and then admixed with portions of 6-chloro-7,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine (W2.006a, 100 mg), suspended in (S)-butan-2-ol (2 ml) and DMF (2 ml). After stirring at 55° C. for 1 h, the mixture was admixed with water and extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate and, after the desiccant had been filtered off, dried under reduced pressure. 105 mg of the title compound were isolated in sufficient purity. LC-MS rt: 0.81 min [M+H]+: 236.2 (met. b)

후처리

  1. customThe suspension formed
  2. temperaturewas heated to 55° C. for 1.5 h
  3. stirringAfter stirring at 55° C. for 1 h
  4. extractionextracted three times with dichloromethane
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationafter the desiccant had been filtered off
  7. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-b38adaf1829d4495893511c6682d3116
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09079906B2

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