Trifluoroacetic acid → HCID 71542038, compound

HRID 1023192Notes

Reaction equation

HRID 1023192 reaction equation
[F:1][CH:2]([F:34])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:15]([CH3:16])[C:14]([CH2:17][CH2:18][C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[N:24](C3CCCCO3)[N:23]=[CH:22]4)=[N:13][N:12]=2)=[CH:6][CH:5]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:24]1[C:25]2[C:21](=[CH:20][C:19]([CH2:18][CH2:17][C:14]3[N:15]([CH3:16])[C:11]([NH:10][C:7]4[CH:8]=[CH:9][C:4]([O:3][CH:2]([F:1])[F:34])=[CH:5][CH:6]=4)=[N:12][N:13]=3)=[CH:27][CH:26]=2)[CH:22]=[N:23]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86680431HCID 86680431, compound

Product 1

HCID 71542038HCID 71542038, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-(4-(difluoromethoxy)phenyl)-4-methyl-5-(2-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)ethyl)-4H-1,2,4-triazol-3-amine (131 mg, 0.280 mmol) in DCM (2 mL), was added TFA (0.646 mL, 8.39 mmol) and the reaction was stirred at room temperature overnight. Solvents were concentrated and the crude product was purified by preparative HPLC on a Sunfire C18 column (150×19×5.0 m) using a gradient of ACN in 10 mM ammonium acetate (0-100%) to give 5-(2-(1H-indazol-5-yl)ethyl)-N-(4-(difluoromethoxy)phenyl)-4-methyl-4H-1,2,4-triazol-3-amine as off white solid (0.026 g, 23%). 1HNMR: 400 MHz, DMSO-d6: δ 2.96-2.98 (m, 2H), 3.08-3.10 (m, 2H), 3.34 (s, 3H), 7.07-7.09 (m, 3H), 7.27-7.28 (m, 1H), 7.47-7.49 (m, 3H), 7.63 (s, 1H), 8.00 (s, 1H), 8.57 (s, 1H), 12.98 (s, 1H). LCMS: RT 1.322 min; LCMS (ES-API), m/z 385 (M+H).

Workup

  1. concentrationSolvents were concentrated
  2. customthe crude product was purified by preparative HPLC on a Sunfire C18 column (150×19×5.0 m)

Sources & evidence

ORD record
ord-e6dfc31e92064e039375283c7d544738
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

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