Diisopropylethylamine → HCID 67537431、化合物

HRID 1192444ノート

反応式

HRID 1192444 の反応式
CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:34]([O:38][C:39]([NH:41][C@H:42]([CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:43]([OH:45])=O)=[O:40])([CH3:37])([CH3:36])[CH3:35].[N:53]1([C:59]2[C:60]3[CH:68]=[CH:67][CH:66]=[N:65][C:61]=3[N:62]=[CH:63][N:64]=2)[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1>C1COCC1.CCOC(C)=O>[C:34]([O:38][C:39](=[O:40])[NH:41][CH:42]([CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:43](=[O:45])[N:56]1[CH2:57][CH2:58][N:53]([C:59]2[C:60]3[CH:68]=[CH:67][CH:66]=[N:65][C:61]=3[N:62]=[CH:63][N:64]=2)[CH2:54][CH2:55]1)([CH3:35])([CH3:36])[CH3:37]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 637610Boc-D-phenylalanineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 223085484-(Piperazin-1-yl)pyrido[2,3-d]pyrimidine

生成物 1

HCID 67537431HCID 67537431、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

DIEA (0.74 mL) and HBTU (1.3 g) was added to the solution of (2R)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid (0.092 g) in THF (5 mL) at 0° C. The mixture was stirred at room temperature for 20 minutes, and then 4-piperazin-1-yl-pyrido[2,3-d]pyrimidine (0.31 g) was added. The reaction was stirred at room temperature for 1 hour. 20 mL of EtOAc was added and the organic layer was separated. The aqueous layer extracted with EtOAc (20 mL). The combined organic layer was washed with saturated sodium bicarbonate (20 mL) and dried over sodium sulfate. After removal of solvent, the residue was purified by flash chromatography (10:1=DCM:MeOH) to give [1-benzyl-2-oxo-2-(4-pyrido[2,3-d]pyrimidin-4-yl-piperazin-yl)-ethyl-carbamic acid tert-butyl ester as white foam solid (0.392 g, 58.9%). 1H NMR (CDCl3, 400 MHz) δ 9.11 (br, 1H), 8.92 (s, 1H), 8.15 (d, 1H), 7.40 (m, 1H), 7.20-7.33 (m, 5H), 5.42 (m, 1H), 4.85 (m, 1H), 3.78-3.82 (m, 2H), 3.61-3.70 (m, 2H), 3.50-3.58 (m, 2H), 3.15-3.20 (m, 1H), 3.08-3.12 (m, 2H), 1.42 (s, 9H). Rt 2.23 min. MS (ESI+) [M+H]+463.

後処理

  1. stirringThe reaction was stirred at room temperature for 1 hour
  2. customthe organic layer was separated
  3. extractionThe aqueous layer extracted with EtOAc (20 mL)
  4. washThe combined organic layer was washed with saturated sodium bicarbonate (20 mL)
  5. dry with materialdried over sodium sulfate
  6. customAfter removal of solvent
  7. customthe residue was purified by flash chromatography (10:1=DCM:MeOH)

出典と根拠

ORDレコード
ord-c3ae4c6ad3974b88a40ec30fa37772fa
出典データセット
uspto-grants-2014_03
特許番号
US08680114B2

反応ノート

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