Trifluoroacetic acid → HCID 178511548, compound

HRID 1819449Notes

Reaction equation

HRID 1819449 reaction equation
C([O:5]C(=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]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH:30]=[CH:29][N:28]=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>[NH4+:7].[OH-:5].[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]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH:30]=[CH:29][N:28]=3)[N:17]=2)[CH2:12][CH2:13]1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 57885587[4-({2-[(Isoquinolin-1-ylmethyl)-amino]-5-nitro-pyrimidin-4-ylamino}-methyl)-cyclohexyl]-carbamic acid tert-butyl ester

Product 2

HCID 14923Ammonium HydroxideHCID 178511548HCID 178511548, compoundYield 166.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[4-({2-[(Isoquinolin-1-ylmethyl)-amino]-5-nitro-pyrimidin-4-ylamino}-methyl)-cyclohexyl]-carbamic acid tert-butyl ester (1.64 g, 3.24 mmol) was dissolved in CH2Cl2 (50 mL) and TFA (15 mL) was added. The reaction mixture was stirred at room temperature for 30 min. The reaction mixture was treated with 1M Na2CO3 and the organic phase was separated. The organic phase was dried over Na2SO4 and concentrated. Silica gel purification using a mixture of CH2Cl2:MeOH:NH4OH yielded 1.1 g of the title compound (84%), m/z 406.2 (M−1)+.

Workup

  1. customthe organic phase was separated
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. customSilica gel purification
  5. additiona mixture of CH2Cl2

Sources & evidence

ORD record
ord-ba1d7e57b2d641168380640222282565
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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