Potassium Carbonate → (S)-tert-butyl (1-(2-((2-(1H-1,2,3-triazol-1-yl)ethyl)amino)-5-(3-carbamoyl-4-fluorophenyl)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)carbamate

HRID 2170348노트

반응식

HRID 2170348 반응식
[N:1]1([CH2:6][CH2:7][NH:8][C:9]2[N:14]=[C:13]([C@@H:15]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:16][C:17]3[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=3)[C:12](Br)=[CH:11][N:10]=2)[CH:5]=[CH:4][N:3]=[N:2]1.[C:34]([C:37]1[CH:38]=[C:39](B(O)O)[CH:40]=[CH:41][C:42]=1[F:43])(=[O:36])[NH2:35].C([O-])([O-])=O.[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1(C)C=CC=CC=1.CC(O)C.O>[N:1]1([CH2:6][CH2:7][NH:8][C:9]2[N:14]=[C:13]([C@@H:15]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:16][C:17]3[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=3)[C:12]([C:39]3[CH:40]=[CH:41][C:42]([F:43])=[C:37]([C:34](=[O:36])[NH2:35])[CH:38]=3)=[CH:11][N:10]=2)[CH:5]=[CH:4][N:3]=[N:2]1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 44717530(3-Carbamoyl-4-fluorophenyl)boronic acidHCID 90290212(S)-tert-butyl (1-(2-((2-(1H-1,2,3-triazol-1-yl)ethyl)amino)-5-bromopyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)carbamate

생성물 1

HCID 90290213(S)-tert-butyl (1-(2-((2-(1H-1,2,3-triazol-1-yl)ethyl)amino)-5-(3-carbamoyl-4-fluorophenyl)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)carbamate

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 66631872toluene IPA water용매

반응 조건

온도
120 °C

실험 절차

In a microwave tube were charged with compound 23C (52 mg, 0.1 mmol), (3-carbamoyl-4-fluorophenyl)boronic acid (27 mg, 0.15 mmol), K2CO3 (41 mg, 0.3 mmol), Pd(dppf)Cl2 (5 mg). To the mixture was added 2 mL of Toluene/2-propanol/H2O (3/1/1). The mixture was heated up to 120° C. for 20 min in a Microwave Synthesizer. The mixture was partitioned between ethyl acetate and water. The organic layer was separated and concentrated to afford crude product used for next step without further purification. MS (m/z) 582.73 [M+H]+.

후처리

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. concentrationconcentrated
  4. customto afford crude product
  5. customused for next step without further purification

출처 및 근거

ORD 기록
ord-aeea0dfc57894ec59b56e49d4d221f2f
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09050344B2

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