Diisopropylethylamine → PKI-587

HRID 2094559Notes

Reaction equation

HRID 2094559 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[C:11]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[N:10]=[C:9]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:37])[NH:27][C:28]4[CH:36]=[CH:35][C:31]([C:32](O)=[O:33])=[CH:30][CH:29]=4)=[CH:21][CH:20]=3)[N:8]=2)[CH2:3][CH2:2]1.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.[CH3:71][N:72]([CH3:79])[CH:73]1[CH2:78][CH2:77][NH:76][CH2:75][CH2:74]1>CN1C(=O)CCC1>[CH3:71][N:72]([CH3:79])[CH:73]1[CH2:78][CH2:77][N:76]([C:32]([C:31]2[CH:35]=[CH:36][C:28]([NH:27][C:26]([NH:25][C:22]3[CH:21]=[CH:20][C:19]([C:9]4[N:10]=[C:11]([N:13]5[CH2:18][CH2:17][O:16][CH2:15][CH2:14]5)[N:12]=[C:7]([N:4]5[CH2:3][CH2:2][O:1][CH2:6][CH2:5]5)[N:8]=4)=[CH:24][CH:23]=3)=[O:37])=[CH:29][CH:30]=2)=[O:33])[CH2:75][CH2:74]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 417391N,N-Dimethylpiperidin-4-amineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 445163074-(3-(4-(4,6-Dimorpholino-1,3,5-triazin-2-yl)phenyl)ureido)benzoic acid

Product 1

HCID 44516953PKI-587Yield 52%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To the solution of 4-(3-(4-(4,6-dimorpholino-1,3,5-triazin-2-yl)phenyl)ureido)benzoic acid (50 mg; 0.099 mmol), Hunig's base (103 μL, 0.594 mmol), HBTU (188 mg, 0.495 mmol) in 2 mL of NMP was reacted according to example 68 with N,N-dimethylpiperidin-4-amine (51 mg, 0.396 mmol). Evaporated the solvent and purified by HPLC to give the product (30.6 mg, 52% yield); MS (ESI) m/z=616.7

Workup

  1. customEvaporated the solvent
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-6c722f54b02e42bb999b05233cb6d80d
Source dataset
uspto-grants-2013_05
Patent number
US08445486B2

Reaction notes

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