Methyl iodide → [2-Methylsulfanyl-7-(3-trifluoromethyl-pyridin-2-yl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-yl]-(4-trifluoromethyl-phenyl)-amine

HRID 1485347ノート

反応式

HRID 1485347 の反応式
[CH3:1][S:2][C:3]1[N:4]=[C:5](O)[C:6]2[CH2:12][CH2:11][N:10]([C:13]3[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:16]=[CH:15][N:14]=3)[CH2:9][CH2:8][C:7]=2[N:23]=1.C(OC(C1C(=O)CCN([C:38]2[C:43]([C:44]([F:47])([F:46])[F:45])=[CH:42][CH:41]=[CH:40][N:39]=2)CC1)=O)C.[CH3:48]C[O-].[Na+].NC(N)=S.CI>CCO>[CH3:1][S:2][C:3]1[N:4]=[C:5]([NH:39][C:40]2[CH:41]=[CH:42][C:43]([C:44]([F:45])([F:46])[F:47])=[CH:38][CH:48]=2)[C:6]2[CH2:12][CH2:11][N:10]([C:13]3[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:16]=[CH:15][N:14]=3)[CH2:9][CH2:8][C:7]=2[N:23]=1

参加物

7

反応物 5

HCID 6328Methyl iodideHCID 2723790ThioureaHCID 2723922Sodium ethoxideHCID 589727845-Oxo-1-(3-trifluoromethyl-pyridin-2-yl)-azepane-4-carboxylic acid ethyl esterHCID 178503519HCID 178503519、化合物

生成物 1

HCID 58972614[2-Methylsulfanyl-7-(3-trifluoromethyl-pyridin-2-yl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-yl]-(4-trifluoromethyl-phenyl)-amine収率 99%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

2-Methylsulfanyl-7-(3-trifluoromethyl-pyridin-2-yl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-ol. To solution of 5-oxo-1-(3-trifluoromethyl-pyridin-2-yl)-azepane-4-carboxylic acid ethyl ester (3.0 g, 9.09 mmol) in EtOH (40 mL) was added NaOEt (1.97 g, 29.1 mmol) and thiourea (1.1 g, 13.6 mmol). The mixture was heated at reflux for 12 h. The mixture was cooled, treated with MeI (0.74 mL, 11.8 mmol) drop-wise, and stirred at rt for 1 h. The mixture was concentrated and the residue was dissolved in water and acidified to pH=7 with HOAc (a precipitate formed). The solid was filtered to give the title compound (3.3 g, >99%), which was used in the next step without further purification.

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 12 h
  3. temperatureThe mixture was cooled
  4. concentrationThe mixture was concentrated
  5. dissolutionthe residue was dissolved in water
  6. customformed)
  7. filtrationThe solid was filtered

出典と根拠

ORDレコード
ord-aa59ac72e2664615b10d01acd8ef0d7e
出典データセット
uspto-grants-2016_08
特許番号
US09422293B2

反応ノート

読み込み中…