Acetic Acid → HCID 178473890、化合物

HRID 1852824ノート

反応式

HRID 1852824 の反応式
[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]

参加物

7

反応物 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、化合物

生成物 1

HCID 178473890HCID 178473890、化合物

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c83bcd7c5fac49568212e0fb76b4ad6a
出典データセット
uspto-grants-2015_02
特許番号
US08962611B2

反応ノート

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