Ammonium formate → (4-Fluoro-1-tetrahydropyran-2-yl-benzimidazol-5-yl)methanamine

HRID 475231ノート

反応式

HRID 475231 の反応式
[F:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[CH:17]=[N:18]O.C([O-])=O.[NH4+]>CO.[Zn]>[F:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:17][NH2:18]

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 866947334-fluoro-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carbaldehyde oxime

生成物 1

HCID 86694734(4-Fluoro-1-tetrahydropyran-2-yl-benzimidazol-5-yl)methanamine収率 47.4%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 887Methanol溶媒

反応条件

温度
75 °C

実験手順

To a solution of 150 (5.8 g, 0.022 mol) in MeOH (100 mL) was added zinc dust (2.9 g, 0.044 mol) and ammonium formate (2.8 g, 0.044 mol). The resulting mixture was heated to 75° C. for 2 h. The mixture was filtered through a Celite® pad. The filtrate was concentrated and the crude product was purified by SiO2 chromatography eluting with 5% MeOH/DCM to afford 2.6 g (47%) of (4-fluoro-1-tetrahydropyran-2-yl-benzimidazol-5-yl)methanamine (152) as a yellow solid: 1H-NMR (400 MHz, RT, CDCl3): δ 1.66-1.80 (m, 3H), 1.92-1.96 (m, 1H), 2.06-2.14 (m, 2H), 3.68-3.74 (m, 1H), 4.23-4.26 (m, 1H), 4.40 (br, 2H), 5.49-5.52 (dd, 1H), 6.94-6.99 (dd, 1H), 7.18-7.23 (t, 1H), and 7.37-7.39 (d, 1H); MS (ESI) m/z=250.2 [M+1]+.

後処理

  1. filtrationThe mixture was filtered through a Celite® pad
  2. concentrationThe filtrate was concentrated
  3. customthe crude product was purified by SiO2 chromatography
  4. washeluting with 5% MeOH/DCM

出典と根拠

ORDレコード
ord-7cc31387f4a1417bb5ceb9d19b2ef9da
出典データセット
uspto-grants-2014_01
特許番号
US08637537B2

反応ノート

読み込み中…