Piperazine → HCID 59376848, compound

HRID 1036159Notes

Reaction equation

HRID 1036159 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][C:17]=2[NH:25][C:26]2[C:27]3[CH:35]=[CH:34][C:33]([CH:36]([CH3:38])[CH3:37])=[N:32][C:28]=3[N:29]=[CH:30][N:31]=2)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CS(C)=O.C(OCC)(=O)C>[CH:36]([C:33]1[CH:34]=[CH:35][C:27]2[C:26]([NH:25][C:17]3[CH:18]=[C:19]([C:20]([N:39]4[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]4)=[O:22])[CH:23]=[CH:24][C:16]=3[S:15][C:12]3[CH:13]=[CH:14][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[CH:10][CH:11]=3)=[N:31][CH:30]=[N:29][C:28]=2[N:32]=1)([CH3:38])[CH3:37]

Participants

7

Reactant 4

HCID 4837PiperazineHCID 81531Diisopropylethylamine2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 593768924-(4-tert-Butoxycarbonylamino-phenylsulfanyl)-3-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-benzoic acid2×

Product 1

HCID 59376848HCID 59376848, compoundYield 133%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product from Example 1E (100 mg, 0.188 mmol) in DMSO (2.0 mL) were added piperazine (16 mg, 0.188 mmol), HATU (79 mg, 0.207 mmol) and Hunigs base (100 μL, 0.564 mmol) and the mixture was stirred at room temperature until the starting material was consumed. Additional product from Example 1E (100 mg, 0.188 mmol), HATU (79 mg, 0.212 mmol), and Hunigs base (100 μL, 0.564 mmol), were added and the reaction was stirred for 2 hours. The reaction was diluted with ethyl acetate and washed water. Dried over Na2SO4, filtered and evaporated. Purification by chromatography on silica gel eluting with (10% methanol in dichloromethane) gave the title compound (150 mg) as a yellow solid.

Workup

  1. customwas consumed
  2. stirringthe reaction was stirred for 2 hours
  3. washwashed water
  4. dry with materialDried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by chromatography on silica gel eluting with (10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-1951dab839684ce393865be0223da541
Source dataset
uspto-grants-2013_10
Patent number
US08546405B2

Reaction notes

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