Diisopropylethylamine → HCID 67537431, compound

HRID 1192444Notes

Reaction equation

HRID 1192444 reaction equation
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]

Participants

7

Reactant 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

Product 1

HCID 67537431HCID 67537431, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-c3ae4c6ad3974b88a40ec30fa37772fa
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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