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

HRID 1404210

반응식

HRID 1404210 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
40 °C

실험 절차

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.

후처리

  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))

출처 및 근거

ORD 기록
ord-f0723d4df4b345f88dcd90055ab0048d
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912224B2

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