Diisopropylethylamine → (4-{[5-Cyano-2-(2-trifluoromethoxy-benzylamino)-pyrimidin-4-ylamino]-methyl}-cyclohexyl)-carbamic acid tert-butyl ester

HRID 1819415Notes

Reaction equation

HRID 1819415 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][C:19]([F:22])([F:21])[F:20])[N:3]=1.[NH2:23][CH2:24][C@H:25]1[CH2:30][CH2:29][C@H:28]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:27][CH2:26]1.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[C:34]([O:33][C:32](=[O:38])[NH:31][CH:28]1[CH2:27][CH2:26][CH:25]([CH2:24][NH:23][C:2]2[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([NH:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[O:18][C:19]([F:22])([F:21])[F:20])[N:3]=2)[CH2:30][CH2:29]1)([CH3:37])([CH3:35])[CH3:36]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 58325043(4-Chloro-5-cyanopyrimidin-2-yl)-(2-trifluoromethoxy-benzyl)-amineHCID 178453944HCID 178453944, compound

Product 1

HCID 59845679(4-{[5-Cyano-2-(2-trifluoromethoxy-benzylamino)-pyrimidin-4-ylamino]-methyl}-cyclohexyl)-carbamic acid tert-butyl esterYield 96%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(4-Chloro-5-cyanopyrimidin-2-yl)-(2-trifluoromethoxy-benzyl)-amine (50 mg, 0.16 mmol) was dissolved in DMF (1 mL) and tert-butyl trans-4-aminomethylcyclohexylcarbamate (70 mg, 0.30 mmol) was added followed by DIPEA (53 μL, 0.30 mmol). The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was then diluted with EtOAc and washed with water (×3). The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. The resulting residue was purified by silica gel preparative TLC using 95:5 CH2Cl2:MeOH as an eluent to afford 76 mg (96%) of (4-{[5-cyano-2-(2-trifluoromethoxy-benzylamino)-pyrimidin-4-ylamino]-methyl}-cyclohexyl)-carbamic acid tert-butyl ester.

Workup

  1. washwashed with water (×3)
  2. dry with materialThe organic phase was dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified by silica gel preparative TLC

Sources & evidence

ORD record
ord-605abb0bc0184541975dd81dffa5d767
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

Loading…