Hydrochloric Acid → HCID 46200199, compound

HRID 1930545Notes

Reaction equation

HRID 1930545 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([NH:22][C:23]2[N:24]=[C:25](OS(C(F)(F)F)(=O)=O)[C:26]3[CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29][C:27]=3[N:28]=2)[CH:13]=[CH:14][C:15]=1[N:16]1[CH:20]=[C:19]([CH3:21])[N:18]=[CH:17]1.Cl>CN(C=O)C>[CH3:8][O:9][C:10]1[CH:11]=[C:12]([NH:22][C:23]2[N:24]=[C:25]([NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:26]3[CH2:32][NH:31][CH2:30][CH2:29][C:27]=3[N:28]=2)[CH:13]=[CH:14][C:15]=1[N:16]1[CH:20]=[C:19]([CH3:21])[N:18]=[CH:17]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 59333814HCID 59333814, compound

Product 1

HCID 46200199HCID 46200199, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Aniline (0.032 g, 0.34 mmol) was added to a solution of tert-butyl 2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-4-(trifluoromethylsulfonyloxy)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (0.2 g, 0.34 mmol, Example 7a) in DMF (2 mL). The solution was stirred at 70° C. for 1 h. HCl 2M aq (2 ml) was added and the solution heated to 76° C. for 1 h. Solvent was concentrated under reduced pressure and purified on preparative HPLC to give N2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-N4-phenyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine (0.060 g, 41.0%). MS (ESI+)/(ESI−) m/z 428/426

Workup

  1. temperaturethe solution heated to 76° C. for 1 h
  2. concentrationSolvent was concentrated under reduced pressure
  3. custompurified on preparative HPLC

Sources & evidence

ORD record
ord-b5bbb272293f4d9b87d083c3ddf0a18c
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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