Trifluoroacetic acid → HCID 178489105, compound

HRID 861167Notes

Reaction equation

HRID 861167 reaction equation
C(OC([NH:8][C:9]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]1[N:29]2[N:30]=[C:31]([C:45]3[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=3)[C:32]([C:33]3[CH:38]=[CH:37][N:36]=[C:35]([NH:39][CH:40]4[CH2:44][CH2:43][CH2:42][CH2:41]4)[N:34]=3)=[C:28]2[CH:27]=[CH:26][CH:25]=1)=[N:10]C(OC(C)(C)C)=O)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH:40]1([NH:39][C:35]2[N:34]=[C:33]([C:32]3[C:31]([C:45]4[CH:46]=[CH:47][C:48]([O:51][CH3:52])=[CH:49][CH:50]=4)=[N:30][N:29]4[C:24]([NH:23][CH2:22][CH2:21][CH2:20][CH2:19][NH:18][C:9]([NH2:10])=[NH:8])=[CH:25][CH:26]=[CH:27][C:28]=34)[CH:38]=[CH:37][N:36]=2)[CH2:44][CH2:43][CH2:42][CH2:41]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178489104HCID 178489104, compound

Product 1

HCID 178489105HCID 178489105, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N,N″-di-tert-butoxycarbonyl-N′-(4-{[3-[2-(cyclopentylamino)-pyrimidin-4-yl]-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-7-yl]amino}butyl)-guanidine (42 mg, 0.06 mmol) in dichloromethane (8 mL) was added trifluoroacetic acid (2 mL). The resultant solution was stirred for 8 hours and then concentrated in vacuo. The residue was dissolved in dichloromethane and saturated aqueous sodium bicarbonate was added. The organic layer was washed with brine. The aqueous layer was extracted with dichloromethane and the combined organics were dried over sodium sulfate. Filtration and concentration provided N-(4-{[3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-7-yl]amino}butyl)guanidine (10 mg, 33%) as a yellow solid. MS m/z 514 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane
  3. additionsaturated aqueous sodium bicarbonate was added
  4. washThe organic layer was washed with brine
  5. extractionThe aqueous layer was extracted with dichloromethane
  6. dry with materialthe combined organics were dried over sodium sulfate
  7. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-c15ec04545944763804bc7b3aedf8de5
Source dataset
uspto-grants-2006_12
Patent number
US07153855B2

Reaction notes

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