Triethylamine → N-[(3-Fluorophenyl)-methyl]-4-methyl-6-morpholin-4-yl-2-pyrrolidin-1-yl-pyridine-3-carboxylic acid amide

HRID 922035ノート

反応式

HRID 922035 の反応式
Cl[C:2]1[C:7]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[O:9])=[C:6]([CH3:19])[CH:5]=[C:4]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[N:3]=1.[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1.CCN(CC)CC>CC#N>[F:18][C:14]1[CH:13]=[C:12]([CH2:11][NH:10][C:8]([C:7]2[C:2]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[N:3][C:4]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[CH:5][C:6]=2[CH3:19])=[O:9])[CH:17]=[CH:16][CH:15]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 866643172-chloro-N-[(3-fluorophenyl)-methyl]-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid amide

生成物 1

HCID 67287287N-[(3-Fluorophenyl)-methyl]-4-methyl-6-morpholin-4-yl-2-pyrrolidin-1-yl-pyridine-3-carboxylic acid amide収率 59%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
140 °C

実験手順

To a solution of 254 mg (0.7 mmol) 2-chloro-N-[(3-fluorophenyl)-methyl]-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid amide (synthesis is described in section a) of example 9) in MeCN (0.5 ml) were added 115 μl (1.4 mmol) pyrrolidine and 290 μl (2.1 mmol) NEt3. The RM was heated in the microwave to 120° C. for 30 min and subsequently to 140° C. for 45 min. Then the mixture was filtered through celite and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 2:1), followed by crystallization (hexane/EtOAc) provided 164 mg (0.41 mmol, 59%) N-[(3-Fluorophenyl)-methyl]-4-methyl-6-morpholin-4-yl-2-pyrrolidin-1-yl-pyridine-3-carboxylic acid amide (example 24). [M+H]+ 399.2.

後処理

  1. filtrationThen the mixture was filtered through celite and
  2. concentrationconcentrated in vacuo
  3. customPurification of the residue by CC (hexane/EtOAc 2:1)
  4. customfollowed by crystallization (hexane/EtOAc)

出典と根拠

ORDレコード
ord-b1fd4efb8cc54120aad5c56ed9eee5b8
出典データセット
uspto-grants-2016_03
特許番号
US09278103B2

反応ノート

読み込み中…