Acetic Acid → 1-methyl-1-[(E)-1-[3-(1-quinolin-6-ylcyclopropyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylideneamino]urea

HRID 456117노트

반응식

HRID 456117 반응식
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3([C:14]4[N:18]5[N:19]=[C:20]([C:23](=O)[CH3:24])[CH:21]=[CH:22][C:17]5=[N:16][N:15]=4)[CH2:13][CH2:12]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(O)(=O)C.[CH3:30][N:31]([C:33]([NH2:35])=[O:34])[NH2:32]>CO>[CH3:30][N:31]([C:33]([NH2:35])=[O:34])/[N:32]=[C:23](/[C:20]1[CH:21]=[CH:22][C:17]2[N:18]([C:14]([C:11]3([C:7]4[CH:6]=[C:5]5[C:10](=[CH:9][CH:8]=4)[N:1]=[CH:2][CH:3]=[CH:4]5)[CH2:12][CH2:13]3)=[N:15][N:16]=2)[N:19]=1)\[CH3:24]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 2560041-Amino-1-methylureaHCID 581905101-(3-(1-(Quinolin-6-yl)cyclopropyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone

생성물 1

HCID 509161621-methyl-1-[(E)-1-[3-(1-quinolin-6-ylcyclopropyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylideneamino]urea수율 41%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of 1-[3-(1-quinolin-6-yl-cyclopropyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]-ethanone (30 mg, 0.091 mmol), acetic acid (0.1 mL) and 1-methylhydrazinecarboxamide (16.2 mg, 0.18 mmol) in methanol (5 mL) was stirred at room temperature overnight. The solvent was removed in vacuo and the residue was diluted with DCM, washed with sat. aqueous NaHCO3. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography in silica gel eluting with a CH2Cl2/MeOH gradient to afford the title compound (14.9 mg, 41%) as yellow solid. 1H-NMR (400 MHz, DMSO-d6) δ ppm 8.84 (dd, 1H), 8.30 (d, 1H), 8.22 (d, 1H), 8.13 (d, 1H), 7.94-7.92 (m, 2H), 7.70 (dd, 1H), 7.49 (dd, 1H), 6.64 (s, 2H), 3.21 (s, 3H), 2.16 (s, 3H), 1.78-1.75 (m, 2H), 1.68-1.65 (m, 2H). LCMS (method A): [MH]+=401, tR=4.11 min.

후처리

  1. customThe solvent was removed in vacuo
  2. additionthe residue was diluted with DCM
  3. washwashed with sat. aqueous NaHCO3
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography in silica gel eluting with a CH2Cl2/MeOH gradient

출처 및 근거

ORD 기록
ord-a4f0b75ad9d94535950e3253af9b7e60
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497368B2

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