Dichloromethane → (S)-6-(methyl(1-phenylethyl)amino)-[1,2,4]triazolo[4,3-b]pyridazine-3-carbonitrile

HRID 521579노트

반응식

HRID 521579 반응식
[CH3:1][N:2]([C@H:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:16])[C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([C:12]([NH2:14])=O)=[N:10][N:11]=2)[N:8]=1.C([O-])(O)=O.[Na+].C(Cl)Cl>CN(C=O)C.O=S(Cl)Cl>[CH3:1][N:2]([C@H:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:16])[C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([C:12]#[N:14])=[N:10][N:11]=2)[N:8]=1

참가 물질

6

반응물 3

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 71115968(S)-6-(methyl(1-phenylethyl)amino)-[1,2,4]triazolo[4,3-b]pyridazine-3-carboxamide

생성물 1

HCID 71116017(S)-6-(methyl(1-phenylethyl)amino)-[1,2,4]triazolo[4,3-b]pyridazine-3-carbonitrile

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 24386Thionyl Chloride용매

실험 절차

To a solution of compound (S)-6-(methyl(1-phenylethyl)amino)-[1,2,4]triazolo[4,3-b]pyridazine-3-carboxamide (0.1 g, 0.34 mmol) in 2 mL of DMF, 1 mL of SOCl2 was added dropwise at 0-5° C., the reaction mixture was stirred for 5 h at room temperature. The mixture was poured onto ice (20 mL) and the mixture was neutralized with NaHCO3. DCM (50 mL) was added; the separated organic layer was dried over anhydrous Na2SO4, and concentrated in vacuum. The residue was purified by flash chromatography eluting with PE/EA=5:1 to give product (S)-6-(methyl(1-phenylethyl)amino)-[1,2,4]triazolo[4,3-b]pyridazine-3-carbonitrile as a yellow solid (Compound 9) (60 mg, 64%). LRMS (M+H+) m/z: calcd 279.43; found 279. 1H NMR (300 MHz, CDCl3): δ 7.98-7.94 (d, J=12 Hz, 1H), 7.35-7.30 (m, 5H), 7.11-7.08 (d, J=9 Hz, 1H), 5.77-5.75 (q, 1H), 2.94 (s, 3H), 1.69-1.66 (d, 3H).

후처리

  1. additionThe mixture was poured onto ice (20 mL)
  2. dry with materialthe separated organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuum
  4. customThe residue was purified by flash chromatography
  5. washeluting with PE/EA=5:1

출처 및 근거

ORD 기록
ord-bb53633afe4a475a9a78908f9e51392b
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09328117B2

반응 노트

불러오는 중…