8-(6-amino-4-chloropyridin-2-ylamino)-6-chloro-N-(3-fluoropyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamide → HCID 178507676、化合物

HRID 1943459

反応式

HRID 1943459 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:10]3[N:11]([C:16]([C:19]([NH:21][C:22]4[CH:27]=[CH:26][N:25]=[CH:24][C:23]=4[F:28])=[O:20])=[CH:17][N:18]=3)[N:12]=[C:13](Cl)[CH:14]=2)[CH:5]=[C:4]([Cl:29])[CH:3]=1.[C@H:30]1([NH2:37])[CH2:35][CH2:34][C@H:33]([NH2:36])[CH2:32][CH2:31]1>CN1C(=O)CCC1>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:10]3[N:11]([C:16]([C:19]([NH:21][C:22]4[CH:27]=[CH:26][N:25]=[CH:24][C:23]=4[F:28])=[O:20])=[CH:17][N:18]=3)[N:12]=[C:13]([NH:36][C@H:33]3[CH2:34][CH2:35][C@H:30]([NH2:37])[CH2:31][CH2:32]3)[CH:14]=2)[CH:5]=[C:4]([Cl:29])[CH:3]=1

参加物

4

反応物 2

HCID 596243518-(6-amino-4-chloropyridin-2-ylamino)-6-chloro-N-(3-fluoropyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamideHCID 178511674HCID 178511674、化合物

生成物 1

HCID 178507676HCID 178507676、化合物収率 44.2%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
110 °C

実験手順

A mixture of 8-(6-amino-4-chloropyridin-2-ylamino)-6-chloro-N-(3-fluoropyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamide (42 mg, 0.073 mmol) and trans-cyclohexane-1,4-diamine (74.2 mg, 0.650 mmol) in NMP (0.4 mL) was heated at 110° C. overnight. The reaction mixture was then cooled to room temperature and purified by reversed-phase HPLC. The fractions containing the title compounds were lyophilized to dryness to afford 8-((6-amino-4-chloro-2-pyridinyl)amino)-6-((trans-4-aminocyclohexyl)amino)-N-(3-fluoro-4-pyridinyl)imidazo[1,2-b]pyridazine-3-carboxamide (16.5 mg, 25%). HPLC Rt=2.813 minutes (Chromolith SpeedROD 4.6×50 mm, 10-90% aqueous methanol containing 0.1% TFA, 4 min gradient, monitored at 220 nm), [M+H]=511.

後処理

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. custompurified by reversed-phase HPLC
  3. additionThe fractions containing the title compounds

出典と根拠

ORDレコード
ord-394a6520f00d4ee2bb459b5a86b724e0
出典データセット
uspto-grants-2013_03
特許番号
US08389527B2

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