Diisopropylethylamine → 4-({2-[(5-cyano-1,3-thiazol-2-yl)amino]-6-ethylpyridin-4-yl}methyl)-N-methylpiperazine-1-carboxamide

HRID 1814014ノート

反応式

HRID 1814014 の反応式
Cl[CH2:2][C:3]1[CH:8]=[C:7]([CH2:9][CH3:10])[N:6]=[C:5]([NH:11][C:12]2[S:13][C:14]([C:17]#[N:18])=[CH:15][N:16]=2)[CH:4]=1.[Cl-].[CH3:20][NH:21][C:22]([N:24]1[CH2:29][CH2:28][NH2+:27][CH2:26][CH2:25]1)=[O:23].C(N(C(C)C)C(C)C)C>CS(C)=O.O>[C:17]([C:14]1[S:13][C:12]([NH:11][C:5]2[CH:4]=[C:3]([CH2:2][N:27]3[CH2:28][CH2:29][N:24]([C:22]([NH:21][CH3:20])=[O:23])[CH2:25][CH2:26]3)[CH:8]=[C:7]([CH2:9][CH3:10])[N:6]=2)=[N:16][CH:15]=1)#[N:18]

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 225042962-{[4-(Chloromethyl)-6-ethylpyridin-2-yl]amino}-1,3-thiazole-5-carbonitrileHCID 695511324-Methylcarbamoyl-piperazin-1-ium chloride

生成物 1

HCID 102001074-({2-[(5-cyano-1,3-thiazol-2-yl)amino]-6-ethylpyridin-4-yl}methyl)-N-methylpiperazine-1-carboxamide

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

2-{[4-(Chloromethyl)-6-ethylpyridin-2-yl]amino}-1,3-thiazole-5-carbonitrile (0.113 g, 0.41 mmol) was dissolved in 2 mL DMSO. 1-[(Methylamino)carbonyl]piperazin-4-ium chloride (0.146 g, 0.81 mmol) and N-ethyl-N,N-diisopropylamine (0.283 mL, 1.63 mmol) were added and the solution was stirred for 24 hours. The reaction was diluted with water and the resulting precipitate was filtered and washed with water. The precipitate was purified by flash column chromatography (gradient, 5-10% MeOH/CH2Cl2). The fractions containing the desired compound were concentrated to dryness to afford the desired product 12-4.

後処理

  1. filtrationthe resulting precipitate was filtered
  2. washwashed with water
  3. customThe precipitate was purified by flash column chromatography (gradient, 5-10% MeOH/CH2Cl2)
  4. additionThe fractions containing the desired compound
  5. concentrationwere concentrated to dryness

出典と根拠

ORDレコード
ord-c1c083e1210848f6b8da0a5ef0dcd9f7
出典データセット
uspto-grants-2005_04
特許番号
US06875767B2

反応ノート

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