Trifluoroacetic acid → HCID 178511552, compound

HRID 1819455Notes

Reaction equation

HRID 1819455 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]2[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][N:19]=[C:18]([NH:25][CH2:26][C:27](=[O:34])[N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[N:17]=2)[CH2:10][CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[NH2:7][C@H:8]1[CH2:9][CH2:10][C@H:11]([CH2:14][NH:15][C:16]2[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][N:19]=[C:18]([NH:25][CH2:26][C:27](=[O:34])[N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[N:17]=2)[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 57885726HCID 57885726, compound

Product 1

HCID 178511552HCID 178511552, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4-{[5-Nitro-2-(2-oxo-2-piperidin-1-yl-ethylamino)-pyrimidin-4-ylamino]-methyl}-cyclohexyl)-carbamic acid tert-butyl ester (36 mg, 0.07 mmol) was dissolved in CH2Cl2 (10 mL) and TFA (1 mL) was added to the solution. The reaction mixture was stirred at room temperature for 16 h. The solution was treated with 3M Na2CO3 to pH 9 and the organic phase was separated. The aqueous phase was extracted with CH2Cl2 and the combined organic phase was dried over Na2SO4 and then concentrated. The resulting residue was purified by silica gel prep TLC using 10:1:0.3 CH2Cl2:MeOH:Et3N as an eluent to afford 27 mg of the title compound as a yellow solid (93%), m/z 392.6 [M+1]+.

Workup

  1. customthe organic phase was separated
  2. extractionThe aqueous phase was extracted with CH2Cl2
  3. dry with materialthe combined organic phase was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe resulting residue was purified by silica gel prep TLC

Sources & evidence

ORD record
ord-bd09c7bfdb1a403b9962dfc8d12e9013
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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