Hydrochloric Acid → HCID 178457104, 화합물

HRID 1405314

반응식

HRID 1405314 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[C:19]([N:20]([CH3:24])[CH:21]([CH3:23])[CH3:22])=[N:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([C:25]#[N:26])[CH:16]=4)[N:11]=3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[N:27]([Na])=[N+:28]=[N-:29].Cl>CS(C)=O.O.Br[Zn]Br>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[C:19]([N:20]([CH3:24])[CH:21]([CH3:23])[CH3:22])=[N:18][C:17]4[C:12]([N:11]=3)=[CH:13][CH:14]=[C:15]([C:25]3[NH:29][N:28]=[N:27][N:26]=3)[CH:16]=4)=[CH:7][CH:8]=2)[CH:3]=[N:2]1

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 706542072-(1H-indazol-5-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carbonitrileHCID 178514644HCID 178514644, 화합물

생성물 1

HCID 178457104HCID 178457104, 화합물수율 23%

시약·촉매·용매 3

HCID 24375Zinc bromide (ZnBr2); Zinc Dibromide촉매HCID 679Dimethyl Sulfoxide용매HCID 962Water용매2회

반응 조건

온도
130 °C

실험 절차

To a solution of 2-(1H-indazol-5-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carbonitrile (150 mg, 0.44 mmol) in DMSO (15 ml) was added dibromozinc (50 mg, 0.22 mmol), azidosodium (86 mg, 1.32 mmol), and water (2 ml), and the resulting mixture was stirred overnight at 130° C. in an oil bath. The solution was diluted with water (200 ml) and adjusted to pH 4 with HCl (2N), extracted with ethyl acetate (5×50 ml), dried over anhydrous magnesium, and concentrated in vacuo to give a residue, which was purified by a silica gel column (10% methanol in dichloromethane) to afford 3-(1H-indazol-5-yl)-N-methyl-N-(propan-2-yl)-7-(1H-tetrazol-5-yl)quinoxalin-2-amine as a yellow solid (38.5 mg, 23%).

후처리

  1. extractionextracted with ethyl acetate (5×50 ml)
  2. dry with materialdried over anhydrous magnesium
  3. concentrationconcentrated in vacuo
  4. customto give a residue, which
  5. customwas purified by a silica gel column (10% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-861a1c89cc074420a88955b33776b988
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916561B2

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