Trifluoroacetic acid → HCID 86679769, compound

HRID 77479Notes

Reaction equation

HRID 77479 reaction equation
O1CCCCC1[N:7]1[C:15]2[C:10](=[CH:11][C:12]([CH2:16][CH2:17][C:18]3[N:23]=[CH:22][N:21]=[C:20]([NH:24][C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=4)[N:19]=3)=[CH:13][CH:14]=2)[CH:9]=[N:8]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:7]1[C:15]2[C:10](=[CH:11][C:12]([CH2:16][CH2:17][C:18]3[N:23]=[CH:22][N:21]=[C:20]([NH:24][C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:33])([F:34])[F:32])=[CH:27][CH:26]=4)[N:19]=3)=[CH:13][CH:14]=2)[CH:9]=[N:8]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 866797684-(2-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)ethyl)-N-(4-(trifluoromethyl)phenyl)-1,3,5-triazin-2-amine

Product 1

HCID 86679769HCID 86679769, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 4-(2-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)ethyl)-N-(4-(trifluoromethyl)phenyl)-1,3,5-triazin-2-amine (0.03 g, 0.064 mmol) in DCM (2 mL) cooled to 0° C., TFA (0.025 mL, 0.320 mmol) was added and the reaction mixture was stirred at 23° C. overnight. The reaction mixture was concentrated, washed with diethyl ether, and purified by preparative HPLC on a SY C18 column (20×19 mm) using 0-100% mobile phase B (ACN) in mobile phase A (10 mM NH4OAc) over 17 min to give 4-(2-(1H-indazol-5-yl)ethyl)-N-(4-(trifluoromethyl)phenyl)-1,3,5-triazin-2-amine as a white solid (4 mg, 16%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washwashed with diethyl ether
  3. custompurified by preparative HPLC on a SY C18 column (20×19 mm)
  4. customover 17 min

Sources & evidence

ORD record
ord-ffe8a94bf6044f38b2450b7920966a13
Source dataset
uspto-grants-2014_09
Patent number
US08841301B2

Reaction notes

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