Formaldehyde → HCID 66704201, compound

HRID 424840Notes

Reaction equation

HRID 424840 reaction equation
[CH:1]([C:4]1[N: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:42])[C:33]1[CH:38]=[CH:37][C:36]([CH:39]=O)=[CH:35][C:34]=1[CH3:41].[B][B][B][B][B][B][B][B][B][B].[CH2:53]=O>CO>[CH3:30][O:31][C:32](=[O:42])[C:33]1[CH:38]=[CH:37][C:36]([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:18])[F:17])[N:7]=[N:8][C:4]=3[CH:1]([CH3:3])[CH3:2])=[CH:23][CH:24]=2)[CH3:53])=[CH:35][C:34]=1[CH3:41]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 20134203Methyl 4-formyl-2-methylbenzoateHCID 66704197HCID 66704197, compoundHCID 178419135HCID 178419135, compound2×

Product 1

HCID 66704201HCID 66704201, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a room temperature solution of 6-[5-isopropyl-3-(2-trifluoromethoxy-phenyl)-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-pyridin-3-ylamine (150 mg, 0.369 mmol) in MeOH (6 mL) is added 4-formyl-2-methyl-benzoic acid methyl ester (72 mg, 0.406 mmol), and the mixture is stirred for 10 min. Decaborane (14 mg, 0.0738 mmol) is added. After 2 h, formaldehyde (2.0 mL, 37 wt % in water) is added and the reaction is stirred for 10 minutes. A second portion of decaborane (14 mg, 0.0738 mmol) is added. After 2 h, the reaction is concentrated and the residue is chromatographed (SiO2 40 g, 0% to 20% EtOAc/Hexane to yield 4-[({6-[5-Isopropyl-3-(2-trifluoromethoxy-phenyl)-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-pyridin-3-yl}-methyl-amino)-methyl]-2-methyl-benzoic acid methyl ester (156 mg, 73%). 1H NMR (400 MHz, DMSO) δ 7.77-7.72 (m, 1H), 7.70 (d, 2H, J=7.9 Hz), 7.66-7.61 (m, 1H), 7.59-7.53 (m, 1H), 7.46 (d, 1H, J=8.8 Hz), 7.23-7.19 (m, 2H), 6.37 (d, 1H, J=8.4 Hz), 5.27 (s, 2H), 3.95 (s, 2H), 3.79 (s, 3H), 3.28 (sept, 1H, J=6.6 Hz), 2.47 (s, 6H), 2.32 (s, 3H), 1.28 (d, 6H, J=6.6 Hz).

Workup

  1. waitAfter 2 h
  2. stirringthe reaction is stirred for 10 minutes
  3. waitAfter 2 h
  4. concentrationthe reaction is concentrated
  5. customthe residue is chromatographed (SiO2 40 g, 0% to 20% EtOAc/Hexane

Sources & evidence

ORD record
ord-9dc8ec958d464fc6a90ffc41d187840e
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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