Hydrochloric Acid → HCID 178511542, compound

HRID 1819423Notes

Reaction equation

HRID 1819423 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]([Cl:22])=[CH:20][N:19]=[C:18](Cl)[N:17]=2)[CH2:10][CH2:9]1)(C)(C)C.Cl.[F:26][C:27]([F:38])([F:37])[O:28][C:29]1[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=1[CH2:31][NH2:32]>CCOC(C)=O>[NH2:7][C@H:8]1[CH2:9][CH2:10][C@H:11]([CH2:14][NH:15][C:16]2[C:21]([Cl:22])=[CH:20][N:19]=[C:18]([NH:32][CH2:31][C:30]3[CH:33]=[CH:34][CH:35]=[CH:36][C:29]=3[O:28][C:27]([F:26])([F:37])[F:38])[N:17]=2)[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2777251(2-(Trifluoromethoxy)phenyl)methanamineHCID 57885682{4-[(2,5-Dichloro-pyrimidin-4-ylamino)-methyl]-cyclohexyl}-carbamic acid tert-butyl ester

Product 1

HCID 178511542HCID 178511542, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

The above {4-[(2,5-dichloro-pyrimidin-4-ylamino)-methyl]-cyclohexyl}-carbamic acid tert-butyl ester (97 mg, 0.26 mmol) was dissolved in 2-trifluoromethoxy-benzylamine (2.5 mL) and the mixture was heated to 180° C. for 20 min. The reaction mixture was diluted with EtOAc and poured into 1N HCl solution. The aqueous layer was separated and extracted with EtOAc (×2). The combined organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. The resulting residue was dissolved in CH2Cl2 (2.5 mL) and TFA (2.5 mL) was added. The reaction mixture was stirred at room temperature for 1 h. The mixture was then poured into 10% NaHCO3 and the aqueous layer was extracted with EtOAc (×2). The combined organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. The resulting residue was purified by silica gel preparative TLC using 9:1:0.1 CH2Cl2:MeOH:NH4OH as an eluent to afford 97 mg (87%) of the title compound, m/z 430.5 (M+1)+.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with EtOAc (×2)
  3. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. dissolutionThe resulting residue was dissolved in CH2Cl2 (2.5 mL)
  6. additionTFA (2.5 mL) was added
  7. additionThe mixture was then poured into 10% NaHCO3
  8. extractionthe aqueous layer was extracted with EtOAc (×2)
  9. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  10. concentrationconcentrated in vacuo
  11. customThe resulting residue was purified by silica gel preparative TLC

Sources & evidence

ORD record
ord-0bcef7e28f39414988902da106f3e3c2
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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