6-chloro-N-(3-fluoropyridin-4-yl)-8-(1-methyl-1H-pyrazol-3-ylamino)imidazo[1,2-b]pyridazine-3-carboxamide → HCID 178480435、化合物

HRID 1943426

反応式

HRID 1943426 の反応式
Cl[C:2]1[CH:3]=[C:4]([NH:21][C:22]2[CH:26]=[CH:25][N:24]([CH3:27])[N:23]=2)[C:5]2[N:6]([C:8]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][N:17]=[CH:16][C:15]=3[F:20])=[O:12])=[CH:9][N:10]=2)[N:7]=1.[C@H:28]1([NH2:35])[CH2:33][CH2:32][C@H:31]([NH2:34])[CH2:30][CH2:29]1>CN1C(=O)CCC1>[NH2:34][C@H:31]1[CH2:32][CH2:33][C@H:28]([NH:35][C:2]2[CH:3]=[C:4]([NH:21][C:22]3[CH:26]=[CH:25][N:24]([CH3:27])[N:23]=3)[C:5]3[N:6]([C:8]([C:11]([NH:13][C:14]4[CH:19]=[CH:18][N:17]=[CH:16][C:15]=4[F:20])=[O:12])=[CH:9][N:10]=3)[N:7]=2)[CH2:29][CH2:30]1

参加物

4

反応物 2

HCID 596247206-chloro-N-(3-fluoropyridin-4-yl)-8-(1-methyl-1H-pyrazol-3-ylamino)imidazo[1,2-b]pyridazine-3-carboxamideHCID 178511674HCID 178511674、化合物

生成物 1

HCID 178480435HCID 178480435、化合物収率 72.9%

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 6-chloro-N-(3-fluoropyridin-4-yl)-8-(1-methyl-1H-pyrazol-3-ylamino)imidazo[1,2-b]pyridazine-3-carboxamide 18A (19.9 mg, 0.044 mmol) and trans-cyclohexane-1,4-diamine (47.6 mg, 0.417 mmol) in NMP (0.7 mL) was heated at 110° C. overnight. The reaction mixture was cooled to room temperature and purified by preparative HPLC. The desired fraction was concentrated and lyophilized to give 18B (14.9 mg, 40%) as a brown solid. [M+H]=465. HPLC Peak Rt=2.263 minutes. (Chromolith column 4.6×50 mm eluting with 10-90% aqueous methanol over 4 minutes containing 0.1% TFA, 4 mL/min, monitoring at 220 nm.)

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompurified by preparative HPLC
  3. concentrationThe desired fraction was concentrated

出典と根拠

ORDレコード
ord-74eaa08e9794454ea501704e86691b0e
出典データセット
uspto-grants-2013_03
特許番号
US08389527B2

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