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 1485347노트

반응식

HRID 1485347 반응식
[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

참가 물질

7

반응물 5

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

생성물 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)-amine수율 99%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-aa59ac72e2664615b10d01acd8ef0d7e
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422293B2

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