Triethylamine → HCID 86713600, compound

HRID 2274228Notes

Reaction equation

HRID 2274228 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]1[N:20]=[C:19]([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[C:18]([Cl:27])=[CH:17][N:16]=1)([CH3:4])([CH3:3])[CH3:2].[N:29]([C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:41])([F:40])[F:39])[CH:33]=1)=[C:30]=[O:31].C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]1[N:20]=[C:19]([N:21]2[CH2:26][CH2:25][N:24]([C:30](=[O:31])[NH:29][C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:39])([F:41])[F:40])[CH:33]=3)[CH2:23][CH2:22]2)[C:18]([Cl:27])=[CH:17][N:16]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 86713599HCID 86713599, compound

Product 1

HCID 86713600HCID 86713600, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of tert-butyl(2-((5-chloro-4-(piperazin-1-yl)pyrimidin-2-yl)amino)phenyl)carbamate (28 mg, 0.068 mmol) in DCM (0.7 mL) was added 1-isocyanato-3-(trifluoromethyl)benzene (0.011 mL, 0.082 mmol) and triethylamine (0.015 mL, 0.1 mmol) and the mixture was stirred at 23° C. for 16 h. reaction. The crude reaction mixture was loaded onto silica gel and purified using 0-50% EtOAc/Hexanes gradient to give the title compound (25 mg, 62%). MS (ES+) C27H29ClF3N7O3 requires: 591. Found: 592 [M+H]+

Workup

  1. customreaction
  2. customThe crude reaction mixture
  3. custompurified

Sources & evidence

ORD record
ord-733a5eef77a843a681cac72fcc1ccd97
Source dataset
uspto-grants-2015_09
Patent number
US09126951B2

Reaction notes

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