Trifluoroacetic acid → HCID 57305486, compound

HRID 1783515Notes

Reaction equation

HRID 1783515 reaction equation
[CH:1]([N:4]1[C:9]2=[N:10][C:11](S(C)=O)=[N:12][CH:13]=[C:8]2[CH2:7][NH:6][C:5]1=[O:17])([CH3:3])[CH3:2].[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][CH:28]([OH:31])[CH2:27][CH2:26]2)=[CH:21][CH:20]=1.FC(F)(F)C(O)=O>C(#N)C>[OH:31][CH:28]1[CH2:29][CH2:30][N:25]([C:22]2[CH:23]=[CH:24][C:19]([NH:18][C:11]3[N:10]=[C:9]4[N:4]([CH:1]([CH3:3])[CH3:2])[C:5](=[O:17])[NH:6][CH2:7][C:8]4=[CH:13][N:12]=3)=[CH:20][CH:21]=2)[CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 167921071-(4-Aminophenyl)piperidin-4-olHCID 54030904HCID 54030904, compound

Product 1

HCID 57305486HCID 57305486, compoundYield 14.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Prepared from 200 mg (0.79 mmol) of 1-isopropyl-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one, 302 mg (1.57 mmol) of 1-(4-aminophenyl)-4-hydroxypiperidine and 182 μL (2.36 mmol) of trifluoroacetic acid in 3.2 mL of acetonitrile. After the workup, the crude residue is triturated in ethyl acetate/dichloromethane and filtered. The filtrate is concentrated further to produce a second crop of crystals. The two are combined and dried to give 45 mg (13%) of the title compound: mp>120° C. (dec).

Workup

  1. customAfter the workup, the crude residue is triturated in ethyl acetate/dichloromethane
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated further
  4. customto produce a second crop of crystals
  5. customdried

Sources & evidence

ORD record
ord-032065e1bb9c4f3c9e856d61dba1c36b
Source dataset
uspto-grants-2009_03
Patent number
US07501425B1

Reaction notes

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