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tert-Butyl isocyanate → 1-tert-butyl-3-(2-{(4S)-6-(3-methylphenyl)-1-oxo-7-[3-(trifluoromethoxy)phenyl]-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl}ethyl)urea

HRID 711416
ノート
印刷プレビュー

反応式

HRID 711416 の反応式
ClC1C=C(C2C=C3C(=O)NCC(CNC(NCC4N5C=C(C6C=CC=C(Cl)C=6)C=C5C(=O)NC4)=O)N3C=2)C=CC=1.Cl.[NH2:42][CH2:43][CH2:44][C@@H:45]1[N:50]2[C:51]([C:65]3[CH:70]=[CH:69][CH:68]=[C:67]([CH3:71])[CH:66]=3)=[C:52]([C:54]3[CH:59]=[CH:58][CH:57]=[C:56]([O:60][C:61]([F:64])([F:63])[F:62])[CH:55]=3)[CH:53]=[C:49]2[C:48](=[O:72])[NH:47][CH2:46]1.[C:73]([N:77]=[C:78]=[O:79])([CH3:76])([CH3:75])[CH3:74].CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl.C(OCC)(=O)C>[C:73]([NH:77][C:78]([NH:42][CH2:43][CH2:44][C@@H:45]1[N:50]2[C:51]([C:65]3[CH:70]=[CH:69][CH:68]=[C:67]([CH3:71])[CH:66]=3)=[C:52]([C:54]3[CH:59]=[CH:58][CH:57]=[C:56]([O:60][C:61]([F:64])([F:62])[F:63])[CH:55]=3)[CH:53]=[C:49]2[C:48](=[O:72])[NH:47][CH2:46]1)=[O:79])([CH3:76])([CH3:75])[CH3:74]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 62412tert-Butyl isocyanateHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 867325541,3-Bis{[7-(3-chlorophenyl)-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl]methyl}ureaHCID 86732565(4S)-4-(2-aminoethyl)-6-(3-methylphenyl)-7-[3-(trifluoromethoxy)phenyl]-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one hydrochloride

生成物 1

HCID 71523270
1-tert-butyl-3-(2-{(4S)-6-(3-methylphenyl)-1-oxo-7-[3-(trifluoromethoxy)phenyl]-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl}ethyl)urea
収率 35%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

28 mg (0.065 mmol) of 1 (4S)-4-(2-aminoethyl)-6-(3-methylphenyl)-7-[3-(trifluoromethoxy)phenyl]-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one hydrochloride were dissolved in 2 ml of DCM. To the obtained solution, 20 μl (0.20 mmol) of t-butyl isocyanate, 60 μl (0.33 mmol) of DIPEA, were added. The mixture was stirred at rt for 18 hours, the solution was portioned between ethyl acetate and saturated aqueous solution of NaHCO3, the organic layer was washed with brine, dried over Na2SO4 and evaporated under vacuum. The crude was purified by HPLC preparative method 1, to provide 1-tert-butyl-3-(2-{(4S)-6-(3-methylphenyl)-1-oxo-7-[3-(trifluoromethoxy)phenyl]-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl}ethyl)urea 12 mg (35%) as a white solid.

後処理

  1. washthe organic layer was washed with brine
  2. dry with materialdried over Na2SO4
  3. customevaporated under vacuum
  4. customThe crude was purified by HPLC preparative method 1

出典と根拠

ORDレコード
ord-cecc709c9a7447e98f51d37991161a6c
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09181258B2

反応ノート

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