Acetic Acid → HCID 178473890, 화합물

HRID 81218노트

반응식

HRID 81218 반응식
[C:1]([OH:4])(=O)[CH3:2].C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:38][C:39]1[CH:40]=[C:41]([C:45]2[C:50]3[N:51]([CH2:63][C@H:64]4[CH2:69][CH2:68][C@H:67]([CH3:70])[CH2:66][CH2:65]4)[C:52]([N:54]4[CH2:59][CH2:58][NH:57][C@@H:56]5[CH2:60][CH2:61][CH2:62][C@@H:55]45)=[N:53][C:49]=3[CH:48]=[C:47]([C:71]#[N:72])[N:46]=2)[CH:42]=[N:43][CH:44]=1>CS(C)=O.CCOC(C)=O>[C:1]([N:57]1[CH2:58][CH2:59][N:54]([C:52]2[N:51]([CH2:63][C@H:64]3[CH2:69][CH2:68][C@H:67]([CH3:70])[CH2:66][CH2:65]3)[C:50]3[C:45]([C:41]4[CH:42]=[N:43][CH:44]=[C:39]([Cl:38])[CH:40]=4)=[N:46][C:47]([C:71]#[N:72])=[CH:48][C:49]=3[N:53]=2)[C@@H:55]2[CH2:62][CH2:61][CH2:60][C@@H:56]12)(=[O:4])[CH3:2]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178461213HCID 178461213, 화합물

생성물 1

HCID 178473890HCID 178473890, 화합물

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

실험 절차

Acetic acid (60.7 mg, 1.01 mmol), N,N-diisopropylethylamine (174 mg, 1.348 mmol) and HATU (513 mg, 1.348 mmol) were added to 4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[(4aR,7aR)-octahydro-1H-cyclopenta[b]pyrazin-1-yl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile (177 mg, 0.33 mmol) in DMSO (1.5 ml), and the mixture was stirred at room temperature overnight. The reaction was then diluted with EtOAc, washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with EtOAc/isohexane to give 2-[(4aR,7aR)-4-acetyloctahydro-1H-cyclopenta[b]pyrazin-1-yl]-4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile. MS ESI calc'd. for C29H34ClN7O [M+H]+ 532. found 532.

후처리

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel
  6. washeluting with EtOAc/isohexane

출처 및 근거

ORD 기록
ord-67980d4443b44de38e9da6ec02d549af
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846657B2

반응 노트

불러오는 중…