Formaldehyde → 3-[({6-[4-Isopropyl-2-(2-trifluoromethoxy-phenyl)-2H-pyrazol-3-ylmethoxy]-2-methyl-pyridin-3-yl}-methyl-amino)-methyl]-benzoic acid methyl ester

HRID 2261855Notes

Reaction equation

HRID 2261855 reaction equation
[CH:1]([C:4]1[CH:8]=[N:7][N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][C:16]([F:19])([F:18])[F:17])[C:5]=1[CH2:20][O:21][C:22]1[N:27]=[C:26]([CH3:28])[C:25]([NH2:29])=[CH:24][CH:23]=1)([CH3:3])[CH3:2].[CH3:30][O:31][C:32](=[O:41])[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH:39]=O)[CH:34]=1.[B][B][B][B][B][B][B][B][B][B].[CH2:52]=O>CO>[CH3:30][O:31][C:32](=[O:41])[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39][N:29]([C:25]2[C:26]([CH3:28])=[N:27][C:22]([O:21][CH2:20][C:5]3[N:6]([C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[O:15][C:16]([F:19])([F:17])[F:18])[N:7]=[CH:8][C:4]=3[CH:1]([CH3:3])[CH3:2])=[CH:23][CH:24]=2)[CH3:52])[CH:34]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 639145Methyl 3-formylbenzoateHCID 675280466-[4-Isopropyl-2-(2-trifluoromethoxy-phenyl)-2H-pyrazol-3-ylmethoxy]-2-methyl-pyridin-3-ylamineHCID 178419135HCID 178419135, compound2×

Product 1

HCID 675279973-[({6-[4-Isopropyl-2-(2-trifluoromethoxy-phenyl)-2H-pyrazol-3-ylmethoxy]-2-methyl-pyridin-3-yl}-methyl-amino)-methyl]-benzoic acid methyl esterYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an ambient temperature solution of 6-[4-isopropyl-2-(2-trifluoromethoxy-phenyl)-2H-pyrazol-3-ylmethoxy]-2-methyl-pyridin-3-ylamine (100 mg, 0.246 mmol) in MeOH (3 mL) is added 3-formyl-benzoic acid methyl ester (40 mg, 0.246 mmol). The reaction mixture is stirred at room temperature for 10 min. Decaborane (12 mg, 0.0738 mmol) is added and the reaction mixture is stirred at room temperature. After 2 h, formaldehyde (2.0 mL, 37 wt % in water) is added and the reaction mixture is stirred at room temperature for 10 min. Decaborane (12 mg, 0.0738 mmol) is added and the reaction is stirred at room temperature. After 2 h, the reaction mixture is concentrated and the residue is chromatographed (SiO2 40 g, 0% to 20% EtOAc/Hex) to yield the title compound (97 mg, 69%). 1H NMR (400 MHz, DMSO) δ 7.91-7.88 (m, 1H), 7.81 (dt, 1H, J=4.6, 2.5 Hz), 7.63 (s, 1H), 7.59-7.50 (m, 4H), 7.48-7.41 (m, 3H), 6.39 (d, 1H, J=7.9 Hz), 5.13 (s, 2H), 4.00 (s, 2H), 3.82 (s, 3H), 3.03 (sept, 1H, J=6.6 Hz), 2.46 (s, 3H), 2.32 (s, 3H), 1.18 (d, 6H, J=6.6 Hz).

Workup

  1. stirringthe reaction mixture is stirred at room temperature
  2. waitAfter 2 h
  3. stirringthe reaction mixture is stirred at room temperature for 10 min
  4. stirringthe reaction is stirred at room temperature
  5. waitAfter 2 h
  6. concentrationthe reaction mixture is concentrated
  7. customthe residue is chromatographed (SiO2 40 g, 0% to 20% EtOAc/Hex)

Sources & evidence

ORD record
ord-9b833ea62b2a42efb35766051253fbf6
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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