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Potassium Carbonate → 3-(6-(aminomethyl)pyridin-3-yl)-N-butylimidazo[1,2-b]pyridazin-6-amine acetic acid salt

HRID 870670
ノート
印刷プレビュー

反応式

HRID 870670 の反応式
[CH2:1]([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([C:12](B(O)O)=[CH:13][N:14]=2)[N:11]=1)[CH2:2][CH2:3][CH3:4].Br[C:19]1[CH:20]=[CH:21][C:22]([CH2:25][NH2:26])=[N:23][CH:24]=1.[C:27](=[O:30])([O-])[O-:28].[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(#N)C.O>[C:27]([OH:28])(=[O:30])[CH3:1].[NH2:26][CH2:25][C:22]1[N:23]=[CH:24][C:19]([C:12]2[N:10]3[N:11]=[C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])[CH:7]=[CH:8][C:9]3=[N:14][CH:13]=2)=[CH:20][CH:21]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 49761678(5-Bromopyridin-2-yl)methanamineHCID 86696352(6-(Butylamino)imidazo[1,2-b]pyridazin-3-yl)boronic acid

生成物 1

HCID 866963723-(6-(aminomethyl)pyridin-3-yl)-N-butylimidazo[1,2-b]pyridazin-6-amine acetic acid salt収率 48.6%

試薬・触媒・溶媒 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
触媒
HCID 18373917Acetonitrile--water (1/1)溶媒

反応条件

温度
145 °C

実験手順

To a mixture of (6-(butylamino)imidazo[1,2-b]pyridazin-3-yl)boronic acid (36 mg, 0.15 mmol), (5-bromopyridin-2-yl)methanamine (35 mg, 0.18 mmol), [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (5 mg, 0.01 mmol) and potassium carbonate (31 mg, 0.23 mmol) was added 3:1 acetonitrile/water (3 mL). The resulting mixture was heated at 145° C. (microwave) for 800 s. The reaction was then filtered and concentrated. The residue was dissolved in methanol, and then filtered again. The filtration was finally purified by preparative HPLC to afford 3-(6-(aminomethyl)pyridin-3-yl)-N-butylimidazo[1,2-b]pyridazin-6-amine acetic acid salt (13 mg, 29% yield) as a white solid: 1H NMR (METHANOL-d4) δ: 8.64 (d, J=8.3 Hz, 1H), 7.91 (s, 1H), 7.66 (d, J=9.6 Hz, 1H), 6.77 (d, J=9.9 Hz, 1H), 3.39 (t, J=7.1 Hz, 2H), 1.94 (s, 4H), 1.71 (t, J=7.3 Hz, 2H), 1.41-1.58 (m, 2H), 1.01 (t, J=7.5 Hz, 3H); LRMS (ESI) m/e 297.4 [(M+H)+, calcd for C16H21N6, 297.2].

後処理

  1. filtrationThe reaction was then filtered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in methanol
  4. filtrationfiltered again
  5. filtrationThe filtration
  6. customwas finally purified by preparative HPLC

出典と根拠

ORDレコード
ord-14abbf3adccc4ac0a0adcaa2784d9294
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08969565B2

反応ノート

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