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

HRID 521579ノート

反応式

HRID 521579 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 24386Thionyl Chloride溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-bb53633afe4a475a9a78908f9e51392b
出典データセット
uspto-grants-2016_05
特許番号
US09328117B2

反応ノート

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