Hydrochloric Acid → HCID 44621578, compound

HRID 2093805Notes

Reaction equation

HRID 2093805 reaction equation
[Cl:1][C:2]1[C:3]([NH:20][C:21]2[CH:25]=[C:24]([CH3:26])[N:23](C3CCCCO3)[N:22]=2)=[N:4][C:5]([NH:8][C:9]2[C:17]([CH3:18])=[CH:16][C:12]([C:13]([OH:15])=O)=[C:11]([CH3:19])[CH:10]=2)=[N:6][CH:7]=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.[CH3:66][N:67]([CH3:71])[CH2:68][CH2:69][NH2:70].Cl>CN(C=O)C>[Cl:1][C:2]1[C:3]([NH:20][C:21]2[CH:25]=[C:24]([CH3:26])[NH:23][N:22]=2)=[N:4][C:5]([NH:8][C:9]2[C:17]([CH3:18])=[CH:16][C:12]([C:13]([NH:70][CH2:69][CH2:68][N:67]([CH3:71])[CH3:66])=[O:15])=[C:11]([CH3:19])[CH:10]=2)=[N:6][CH:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 66053N,N-DimethylethylenediamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67168122HCID 67168122, compound

Product 1

HCID 44621578HCID 44621578, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(5-chloro-4-(5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)-2,5-dimethylbenzoic acid (35.0 mg, 0.077 mmol) in DMF (0.5 mL) was added HATU (29.1 mg, 0.077 mmol), DIEA (26.7 μL, 0.153 mmol) and N1,N1-dimethylethane-1,2-diamine (25.2 μL, 0.230 mmol). The reaction mixture was stirred at room temperature overnight. 1N HCl aqueous solution (0.5 mL) was then added and the reaction mixture was heated at 100° C. for 1.5 hours to remove the tetrahydro-2H-pyran-2-yl protecting group. The mixture was purified by preparative RP-HPLC to provide 4-(5-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)-N-(2-(dimethylamino)ethyl)-2,5-dimethylbenzamide; ESMS m/z 443.2 (M+H+).

Workup

  1. temperaturethe reaction mixture was heated at 100° C. for 1.5 hours
  2. customto remove the tetrahydro-2H-pyran-2-yl protecting group
  3. customThe mixture was purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-382953bc65fe462d8dab1af47aad3e83
Source dataset
uspto-grants-2013_05
Patent number
US08445505B2

Reaction notes

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