Trifluoroacetic acid → HCID 178511545, compound

HRID 1819469Notes

Reaction equation

HRID 1819469 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:32]=[CH:31][CH:30]=[C:29]([N:33]4[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]4)[CH:28]=3)[N:17]=2)[CH2:10][CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>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]3[CH:32]=[CH:31][CH:30]=[C:29]([N:33]4[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]4)[CH:28]=3)[N:17]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57885629(4-{[5-Nitro-2-(3-piperidin-1-yl-benzylamino)-pyrimidin-4-ylamino]-methyl}-cyclohexyl)-carbamic acid tert-butyl ester

Product 1

HCID 178511545HCID 178511545, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4-{[5-Nitro-2-(3-piperidin-1-yl-benzylamino)-pyrimidin-4-ylamino]-methyl}-cyclohexyl)-carbamic acid tert-butyl ester (176 mg, 0.33 mmol) was dissolved in CH2Cl2 (6 mL). To this solution was added TFA (3 mL) and the reaction was stirred for 1 h. The volatiles were removed and the crude was re-dissolved in 90:9:1 (CH2Cl2:CH3OH:NH4OH), then concentrated again to afford a solid. The resultant solid was purified via flash chromatography (SiO2, 10-75% CH2Cl2-(90:9:1-CH2Cl2:CH3OH:NH4OH)) to afford 131 mg (91%) of the target compound , m/z 440.72 [M+1]+.

Workup

  1. customThe volatiles were removed
  2. dissolutionthe crude was re-dissolved in 90:9:1 (CH2Cl2:CH3OH:NH4OH)
  3. concentrationconcentrated again
  4. customto afford a solid
  5. customThe resultant solid was purified via flash chromatography (SiO2, 10-75% CH2Cl2-(90:9:1-CH2Cl2:CH3OH:NH4OH))

Sources & evidence

ORD record
ord-573f1bf448bc42688a1b40420ca94cee
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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