Ethyl chloroformate → HCID 16071133, 화합물

HRID 2064214노트

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HRID 2064214 반응식
[Br:1][C:2]1[CH:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH2:11][CH2:10]2)[C:5]([NH2:21])=[CH:4][C:3]=1[C:22]([F:25])([F:24])[F:23].C(N(C(C)C)CC)(C)C.Cl[C:36](OCC)=[O:37]>O1CCCC1>[Br:1][C:2]1[C:3]([C:22]([F:23])([F:25])[F:24])=[CH:4][C:5]2[NH:21][C:36](=[O:37])[N:8]([CH:9]3[CH2:10][CH2:11][N:12]([CH:15]4[CH2:20][CH2:19][O:18][CH2:17][CH2:16]4)[CH2:13][CH2:14]3)[C:6]=2[CH:7]=1

참가 물질

5

반응물 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 59850187HCID 59850187, 화합물

생성물 1

HCID 16071133HCID 16071133, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
150 °C

실험 절차

A stirred solution of 5-bromo-N-[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]-4-(trifluoromethyl)-1,2-benzenediamine (D55) (0.34 mmol) in tetrahydrofuran (8 ml) at room temperature under argon was treated with diisopropylethylamine (0.12 ml, 0.68 mmol) followed by ethyl chloroformate (40 mg, 0.38 mmol) and then heated under reflux for 2 hrs. The mixture was concentrated under vacuum and the residue dissolved in dimethylformamide, treated with more diisopropylethylamine (0.12 ml) and heated at 150° C. for 0.75 hr. The solution was then concentrated under vacuum and the residue treated with 10% Na2CO3 solution and extracted with ethyl acetate. The extract was dried and concentrated under vacuum. The residue was triturated with diethyl ether to afford 6-bromo-1-[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]-5-(trifluoromethyl)-1,3-dihydro-2H-benzimidazol-2-one as a beige solid. This was converted to its HCl salt as a beige solid (55 mg, 33%). MH+=448, 450.

후처리

  1. temperatureheated
  2. temperatureunder reflux for 2 hrs
  3. concentrationThe mixture was concentrated under vacuum
  4. dissolutionthe residue dissolved in dimethylformamide
  5. additiontreated with more diisopropylethylamine (0.12 ml)
  6. concentrationThe solution was then concentrated under vacuum
  7. additionthe residue treated with 10% Na2CO3 solution
  8. extractionextracted with ethyl acetate
  9. customThe extract was dried
  10. concentrationconcentrated under vacuum
  11. customThe residue was triturated with diethyl ether

출처 및 근거

ORD 기록
ord-564f4788d3694b41bfc6a3bb2b3c0053
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288412B2

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