Diisopropylethylamine → 2-ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-4-methyl-6-[methyl-(tetrahydro-pyran-2-yl-methyl)-amino]-pyridine-3-carboxylic acid amide

HRID 922016ノート

反応式

HRID 922016 の反応式
Cl[C:2]1[N:7]=[C:6]([S:8][CH2:9][CH3:10])[C:5]([C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)=[O:12])=[C:4]([CH3:22])[CH:3]=1.[CH3:23][NH:24][CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][O:27]1.CCN(C(C)C)C(C)C>CC#N.[OH-].[Na+].CCOC(C)=O>[CH2:9]([S:8][C:6]1[C:5]([C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)=[O:12])=[C:4]([CH3:22])[CH:3]=[C:2]([N:24]([CH3:23])[CH2:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)[N:7]=1)[CH3:10]

参加物

7

反応物 3

HCID 81531DiisopropylethylamineHCID 12700142N-Methyl-1-(tetrahydro-2H-pyran-2-yl)methanamineHCID 866643146-chloro-2-ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-4-methyl-pyridine-3-carboxylic acid amide

生成物 1

HCID 569627632-ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-4-methyl-6-[methyl-(tetrahydro-pyran-2-yl-methyl)-amino]-pyridine-3-carboxylic acid amide収率 38%

試薬・触媒・溶媒 3

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

A solution of 254 mg (0.75 mmol) 6-chloro-2-ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-4-methyl-pyridine-3-carboxylic acid amide (synthesis is described in section b) of example 2), 322 mg (2.25 mmol) N-methyl-1-(tetrahydro-2H-pyran-2-yl)methanamine and 392 μl (2.25 mmol) DIPEA in MeCN (2 ml) was heated in the microwave at 150° C. for 4.5 h. Subsequently the RM was diluted with a 2M aq. NaOH sol and EtOAc and the layers were separated. The organic layer was washed with water and brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 1:1) provided 122 mg (0.28 mmol, 38%) 2-ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-4-methyl-6-[methyl-(tetrahydro-pyran-2-yl-methyl)-amino]-pyridine-3-carboxylic acid amide (example 5). [M+H]+ 432.2.

後処理

  1. customthe layers were separated
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by CC (hexane/EtOAc 1:1)

出典と根拠

ORDレコード
ord-cc60a58aad34481e97991b8d7a2b46d9
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…