Trifluoroacetic acid → HCID 178511537, compound

HRID 1819454Notes

Reaction equation

HRID 1819454 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]3[CH:36]=[CH:35][CH:34]=[C:33]4[C:28]=3[CH:29]=[CH:30][CH:31]=[N:32]4)[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[CH2:13][CH2:12][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[CH:36]=[CH:35][CH:34]=[C:33]4[C:28]=3[CH:29]=[CH:30][CH:31]=[N:32]4)[N:17]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 57885717[4-({5-Nitro-2-[(quinolin-5-ylmethyl)-amino]-pyrimidin-4-ylamino}-methyl)-cyclohexyl]-carbamic acid tert-butyl ester

Product 1

HCID 178511537HCID 178511537, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[4-({5-Nitro-2-[(quinolin-5-ylmethyl)-amino]-pyrimidin-4-ylamino}-methyl)-cyclohexyl]-carbamic acid tert-butyl ester (197 mg, 0.39 mmol) was dissolved in CH2Cl2 (10 mL) and TFA (2 mL) was added. The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was treated with 3M Na2CO3 and the organic phase was separated. The organic phase was dried over Na2SO4 and concentrated. Silica gel purification using a mixture of 10:1:0.3 CH2Cl2:MeOH:Et3N yielded 120 mg of the title compound as a light yellow solid (79%), m/z 406.4 [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 10:1:0.3 CH2Cl2

Sources & evidence

ORD record
ord-59007c2d97ef4cc888f8dad698d52635
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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