Ethyl isocyanate → HCID 66628276, 화합물

HRID 1046880노트

반응식

HRID 1046880 반응식
[NH2:1][C:2]1[N:31]=[C:5]2[N:6]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[C:7]([CH3:20])=[C:8]([C:18]#[N:19])[C@@H:9]([C:10]3[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=3)[N:4]2[N:3]=1.S([O-])([O-])(=O)=O.[Na+].[Na+].[CH2:39]([N:41]=[C:42]=[O:43])[CH3:40]>N1C=CC=CC=1>[C:18]([C:8]1[C@@H:9]([C:10]2[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=2)[N:4]2[N:3]=[C:2]([NH:1][C:42]([NH:41][CH2:39][CH3:40])=[O:43])[N:31]=[C:5]2[N:6]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:30])[F:29])[CH:22]=2)[C:7]=1[CH3:20])#[N:19]

참가 물질

5

반응물 3

HCID 8022Ethyl isocyanateHCID 24436Sodium SulfateHCID 66627900HCID 66627900, 화합물

생성물 1

HCID 66628276HCID 66628276, 화합물

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
100 °C

실험 절차

Under an atmosphere of argon protective gas, (7R)-2-amino-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile (15 mg, 33 μmol) was dissolved in abs. pyridine (2 ml), and solid sodium sulfate (spatula tip) and ethyl isocyanate (46.6 mg, 655 μmol, 20 eq.) were added. The reaction mixture was then heated in a microwave reactor (2.5 h at 100° C., then 2 h at 110° C. and finally 2 h at 125° C.). After cooling, the reaction mixture was filtered, the filtrate was concentrated under reduced pressure and the residue was purified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA). After lyophilization, the product was obtained as a solid (7.8 mg, 48% of theory).

후처리

  1. custom2 h
  2. customat 110° C.
  3. customfinally 2 h
  4. customat 125° C.
  5. temperatureAfter cooling
  6. filtrationthe reaction mixture was filtered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA)
  9. customAfter lyophilization, the product was obtained as a solid (7.8 mg, 48% of theory)

출처 및 근거

ORD 기록
ord-fb7ba22d7b074bbeabf031c3a0dd3890
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569314B2

반응 노트

불러오는 중…