Trifluoroacetic acid → HCID 10414747, compound

HRID 459986Notes

Reaction equation

HRID 459986 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:19]3=[N:20][C:21]([NH2:24])=[N:22][CH:23]=[C:18]3[CH2:17][N:16]([C:25]3[C:30]([F:31])=[C:29]([O:32][CH3:33])[CH:28]=[C:27]([O:34][CH3:35])[C:26]=3[F:36])[C:15]2=[O:37])[CH2:10][CH2:9]1)=O)(C)(C)C.[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41]>ClCCl>[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41].[NH2:24][C:21]1[N:20]=[C:19]2[N:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[C:15](=[O:37])[N:16]([C:25]3[C:26]([F:36])=[C:27]([O:34][CH3:35])[CH:28]=[C:29]([O:32][CH3:33])[C:30]=3[F:31])[CH2:17][C:18]2=[CH:23][N:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86590949HCID 86590949, compound

Product 1

HCID 10414747HCID 10414747, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-[7-Amino-3-(2,6-difluoro-3,5-dimethoxy-phenyl)-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (295 mg, 0.567 mmol) in dichloromethane (5 mL) at 0° C. trifluoroacetic acid (647 μL) was added. The resulting solution was stirred at room temperature for 5 hours. The solution was then concentrated under reduced pressure. The resulting residue was concentrated with toluene (2×50 mL) to give a thick oil. Dichloromethane (2 mL) was added to the oil to produce a white precipitate. To accelerate precipitation diethyl ether (10 mL) was added. The mixture was then filtered to deliver 338 mg (92%) of the title compound as a white powder: mp 200° C.–220° C. (decomposition); MS (APCI) 421.1, 422.2.

Workup

  1. concentrationThe solution was then concentrated under reduced pressure
  2. concentrationThe resulting residue was concentrated with toluene (2×50 mL)
  3. customto give a thick oil
  4. customto produce a white precipitate
  5. customprecipitation diethyl ether (10 mL)
  6. additionwas added
  7. filtrationThe mixture was then filtered

Sources & evidence

ORD record
ord-26a17f152a6c4cdaa3ea9b6731e5c25d
Source dataset
uspto-grants-2007_03
Patent number
US07196090B2

Reaction notes

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