4-(Methylamino)pyridine → [2-(2-Phenyl-chroman-6-yloxy)-thiazol-5-ylmethyl]-pyridin-4-ylmethyl-amine

HRID 1404210

反応式

HRID 1404210 の反応式
[C:1]1([CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([O:17][C:18]4[S:19][C:20]([CH:23]=O)=[CH:21][N:22]=4)[CH:13]=3)[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:25]1[CH:30]=[CH:29][C:28](NC)=[CH:27][CH:26]=1.[C:33]([BH3-])#[N:34].[Na+]>O1CCCC1.C(O)(=O)C>[C:1]1([CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([O:17][C:18]4[S:19][C:20]([CH2:23][NH:34][CH2:33][C:28]5[CH:27]=[CH:26][N:25]=[CH:30][CH:29]=5)=[CH:21][N:22]=4)[CH:13]=3)[O:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

6

反応物 3

HCID 1230984-(Methylamino)pyridineHCID 5003444Sodium cyanoborohydrideHCID 866780922-(2-Phenyl-chroman-6-yloxy)-thiazole-5-carbaldehyde

生成物 1

HCID 71292961[2-(2-Phenyl-chroman-6-yloxy)-thiazol-5-ylmethyl]-pyridin-4-ylmethyl-amine収率 53.7%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

To a suspension of 2-(2-phenyl-chroman-6-yloxy)-thiazole-5-carbaldehyde (54 mg, 0.13 mmol) and pyridin-4-yl-methylamine (17 mg, 0.16 mmol, 1.2 eq) in tetrahydrofuran (3 ml) and acetic acid (0.5 ml) at 0° C. sodium cyanoborohydride (polymer bond, 2.19 mM/g, 137 mg, 0.30 mmol, 2.3 eq) was added and the mixture stirred at 40° C. for 16 h. The reaction mixture was filtered, the volatile components removed under reduced pressure and the remaining residue purified by reversed phase HPLC (water/acetonitrile gradient (+0.1% trifluoroacetic acid)) to give 30 mg (42%) of [2-(2-phenyl-chroman-6-yloxy)-thiazol-5-ylmethyl]-pyridin-4-ylmethyl-amine in the form of its salt with trifluoroacetic acid.

後処理

  1. additionwas added
  2. filtrationThe reaction mixture was filtered
  3. customthe volatile components removed under reduced pressure
  4. customthe remaining residue purified by reversed phase HPLC (water/acetonitrile gradient (+0.1% trifluoroacetic acid))

出典と根拠

ORDレコード
ord-f0723d4df4b345f88dcd90055ab0048d
出典データセット
uspto-grants-2014_12
特許番号
US08912224B2

関連ノート

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