Hydrochloric Acid → HCID 178461412、化合物

HRID 2390421ノート

反応式

HRID 2390421 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]#[C:10][CH2:11][CH2:12][N:13]2[CH2:17][CH2:16][CH2:15][C@H:14]2[CH3:18])=[C:6]([NH2:8])[CH:7]=1.Cl.[N:20]([O-])=O.[Na+].[OH2:24]>>[Br:1][C:2]1[CH:7]=[C:6]2[C:5]([C:9]([OH:24])=[C:10]([CH2:11][CH2:12][N:13]3[CH2:17][CH2:16][CH2:15][C@H:14]3[CH3:18])[N:20]=[N:8]2)=[CH:4][CH:3]=1

参加物

5

反応物 4

HCID 313Hydrochloric AcidHCID 962Water2 回HCID 23668193Sodium NitriteHCID 671046725-Bromo-2-[4-((2r)-2-methyl-pyrrolidin-1-yl)-but-1-ynyl]-phenylamine

生成物 1

HCID 178461412HCID 178461412、化合物収率 47%

反応条件

温度
0 °C

実験手順

To a mixture of Example 168C (0.10 g, 0.325 mmol) in 2 mL of water was added 1.5 mL 6 M HCl. The resulting solution was cooled to 0° C. and NaNO2 (0.034 g, 0.488 mmol), dissolved in 1 mL water, was added dropwise. The resulting mixture was stirred for 30 minutes at 0° C. and subsequently heated to 90° C. for one hour. After cooling, contents were filtered and the precipitate was washed with 10 mL water and dried under reduced pressure to provide the product in 47% yield as a brown solid in HCl salt form, which was used without further purification. 1H NMR (CD3OD, 300 MHz) δ 8.10 (d, J=9 Hz, 1H), 7.82 (d, J=3 Hz, 1H), 7.60 (dd, J=3, 9 Hz, 1H), 3.89-3.76 (m, 2H), 3.58-3.53 (m, 1H) 3.42-3.23 (m, 4H), 2.38-2.30 (m, 1H), 2.16-2.06 (m, 2H), 1.83-1.75 (m, 1H), 1.51 (d, J=6 Hz, 3H). MS (ESI) [M]+ at 336.

後処理

  1. additionwas added dropwise
  2. temperaturesubsequently heated to 90° C. for one hour
  3. temperatureAfter cooling
  4. filtrationcontents were filtered
  5. washthe precipitate was washed with 10 mL water
  6. customdried under reduced pressure
  7. customto provide the product in 47% yield as a brown solid in HCl salt form, which
  8. customwas used without further purification

出典と根拠

ORDレコード
ord-bb133299978f47958a1ac1cc28e5d051
出典データセット
uspto-grants-2012_09
特許番号
US08273767B2

反応ノート

読み込み中…