Hydrochloric Acid → HCID 178517557, 화합물

HRID 1295683

반응식

HRID 1295683 반응식
N12CCCN=C1CCCCC2.C(O[C:15](=[O:31])[CH:16]([C:22]1[C:27]([F:28])=[CH:26][C:25]([F:29])=[CH:24][C:23]=1[F:30])[C:17]([O:19]CC)=O)C.Cl.[N:33]1[CH:38]=[CH:37][N:36]=[CH:35][C:34]=1[C:39]([NH2:41])=[NH:40].Cl>CN1CCCC1=O.O>[N:33]1[CH:38]=[CH:37][N:36]=[CH:35][C:34]=1[C:39]1[N:41]=[C:15]([OH:31])[C:16]([C:22]2[C:23]([F:30])=[CH:24][C:25]([F:29])=[CH:26][C:27]=2[F:28])=[C:17]([OH:19])[N:40]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 470895Pyrazine-2-carboxamidine hydrochlorideHCID 2782662Propanedioic acid, 2-(2,4,6-trifluorophenyl)-, 1,3-diethyl ester

생성물 1

HCID 178517557HCID 178517557, 화합물수율 76%

시약·촉매·용매 2

HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
95 °C

실험 절차

1,8-diazabicyclo[5.4.0]undec-7-ene (DBU; 14.4 g, 0.0944 mol) is added to a mixture of 2-(2,4,6-triflorophenyl)malonic acid diethyl ester (14.3 g, 0.0472 mol) and pyrazine-2-carboxamidine hydrochloride (9.00 g, 0.0566 mol) in 1-methyl-2-pyrrolidinone (NMP; 50 mL) solvent. The resulting mixture is heated to 95° C. while stirring for 7 hours. The mixture is cooled to about 50° C. and then HCl solution (37%, 5.6 mL) is added dropwise, keeping the temperature below 50° C. The mixture is then allowed to cool to about 20° C. Water (50 mL) is added dropwise over 20 minutes, causing the product to precipitate as a solid from the mixture (20–25° C.). The solid is collected by filtration, and the product cake is washed with water (300 mL). The solid is allowed to dry at 23° C. under atmospheric pressure for 24 hours, giving a yellow solid (11.5 g, 97% HPLC area, 76% yield. 1H NMR (DMSO-d6): d 12.45 (bs, 2H), 9.41 (s,1H), 8.91(s,1H), 8.46(m, 1H), 7.23(m, 2H).

후처리

  1. temperatureThe mixture is cooled to about 50° C.
  2. customthe temperature below 50° C
  3. temperatureto cool to about 20° C
  4. customto precipitate as a solid from the mixture (20–25° C.)
  5. filtrationThe solid is collected by filtration
  6. washthe product cake is washed with water (300 mL)
  7. customto dry at 23° C. under atmospheric pressure for 24 hours
  8. customgiving a yellow solid (11.5 g, 97% HPLC area, 76% yield

출처 및 근거

ORD 기록
ord-f532b6780e58430599c601d15084fb85
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07244736B2

연결된 노트

불러오는 중…