Tetrahydrofuran → 5,6-difluoro-N-(4-(3-(2-(methylthio)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)-1H-benzo[d]imidazol-2-amine

HRID 252648

반응식

HRID 252648 반응식
[N:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][C:9]2[C:14]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([S:21][CH3:22])[N:16]=3)=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:6][CH:5]=1)=[C:2]=S.C1CCC(N=C=NC2CCCCC2)CC1.[F:40][C:41]1[CH:42]=[C:43]([NH2:49])[C:44]([NH2:48])=[CH:45][C:46]=1[F:47].C1COCC1>C(Cl)Cl>[F:40][C:41]1[C:46]([F:47])=[CH:45][C:44]2[NH:48][C:2]([NH:1][C:4]3[CH:24]=[CH:23][C:7]([O:8][C:9]4[C:14]([C:15]5[CH:20]=[CH:19][N:18]=[C:17]([S:21][CH3:22])[N:16]=5)=[CH:13][CH:12]=[CH:11][N:10]=4)=[CH:6][CH:5]=3)=[N:49][C:43]=2[CH:42]=1

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 10868DicyclohexylcarbodiimideHCID 27367551,2-Diamino-4,5-difluorobenzeneHCID 866149574-(2-(4-Isothiocyanatophenoxy)pyridin-3-yl)-2-(methylthio)pyrimidine

생성물 1

HCID 668627235,6-difluoro-N-(4-(3-(2-(methylthio)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)-1H-benzo[d]imidazol-2-amine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
70 °C

실험 절차

A resealable pressure vial, under nitrogen, was charged with 4-(2-(4-isothiocyanatophenoxy)pyridin-3-yl)-2-(methylthio)pyrimidine (1.12 g, 3.18 mmol), PS-DCC (1.27 mmol/g polymer supported cyclohexyl carbodiimide) (7.50 g, 9.53 mmol), 4,5-difluorobenzene-1,2-diamine (0.69 g, 4.77 mmol), and THF (45 ml, 0.07 M). The vessel was sealed and the reaction mixture stirred at 70° C. for 4 h. The reaction mixture was cooled to RT, diluted with DCM, and filtered over celite. The filtrate was concentrated to afford yellow residue, which was triturated with DCM, filtered, and dried under high vacuum to afford 5,6-difluoro-N-(4-(3-(2-(methylthio)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)-1H-benzo[d]imidazol-2-amine as a tan solid. MS m/z=463.1 [M+H]+. Calc'd for C23H16F2N6OS: 462.48.

후처리

  1. customThe vessel was sealed
  2. temperatureThe reaction mixture was cooled to RT
  3. filtrationfiltered over celite
  4. concentrationThe filtrate was concentrated
  5. customto afford yellow residue, which
  6. customwas triturated with DCM
  7. filtrationfiltered
  8. customdried under high vacuum

출처 및 근거

ORD 기록
ord-e1f3622889764387952ef6c3d4aee72f
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868177B2

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