Dimethylamine → HCID 178483894, compound

HRID 570240Notes

Reaction equation

HRID 570240 reaction equation
[C:1]([C:5]1[C:6]([Cl:34])=[C:7]([C:11]2[NH:33][C:14]3[C:15]([O:29][CH2:30][CH:31]=O)=[N:16][C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:25]([F:28])([F:27])[F:26])=[CH:18][C:13]=3[N:12]=2)[N:8]([CH3:10])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:35][NH:36][CH3:37].C1COCC1.C([BH3-])#N.[Na+]>CCOC(C)=O.CO.CC(O)=O>[C:1]([C:5]1[C:6]([Cl:34])=[C:7]([C:11]2[NH:33][C:14]3[C:15]([O:29][CH2:30][CH2:31][N:36]([CH3:37])[CH3:35])=[N:16][C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:25]([F:26])([F:27])[F:28])=[CH:18][C:13]=3[N:12]=2)[N:8]([CH3:10])[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydrideHCID 178481823HCID 178481823, compound

Product 1

HCID 178483894HCID 178483894, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 10129899Acetic acid methanolSolvent

Procedure

To a mixture of [2-(5-tert-butyl-4-chloro-2-methyl-2H-pyrazol-3-yl)-6-(2-trifluoromethyl-phenyl)-3H-imidazo[4,5-c]pyridin-4-yloxy]-acetaldehyde (40.0 mg, 0.0813 mmol, prepared as described in Example 12, STEP A) in 30:1 MeOH/AcOH (2 mL) was added 2.0 M dimethyl amine in THF (81.3 μL, 0.163 mmol) followed by sodium cyanoborohydride (10.2 mg, 0.163 mmol). After stirring at room temperature for 18 h, the resulting mixture was treated with EtOAc (50 mL) and washed with saturated aqueous NH4Cl (20 mL), H2O (20 mL) and brine (20 mL). The organic layer was dried with Na2SO4 and concentrated in vacuo. The resulting residue was purified by flash chromatography on silica gel (0:100-10:90 MeOH/DCM) to yield {2-[2-(5-tert-Butyl-4-chloro-2-methyl-2H-pyrazol-3-yl)-6-(2-trifluoromethyl-phenyl)-3H-imidazo[4,5-c]pyridin-4-yloxy]-ethyl}-dimethyl-amine as a light yellow solid. 1H-NMR (400 MHz, CD3OD) δ: 7.84 (d, J=7.6 Hz, 1H), 7.67-7.75 (m, 1H), 7.58-7.66 (m, 2H), 7.37-7.43 (m, 1H), 4.80-4.86 (m, 2H), 4.03 (s, 3H), 3.47-3.55 (m, 2H), 2.88 (s, 6H), 1.45 (s, 9H). Mass Spectrum (LCMS, ESI pos.) Calculated For C25H28ClF3N6O: 521.2 (M+H), Measured: 521.2.

Workup

  1. washwashed with saturated aqueous NH4Cl (20 mL), H2O (20 mL) and brine (20 mL)
  2. dry with materialThe organic layer was dried with Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified by flash chromatography on silica gel (0:100-10:90 MeOH/DCM)

Sources & evidence

ORD record
ord-d73ca19778ff437b94b289d760c9fdba
Source dataset
uspto-grants-2015_05
Patent number
US09023846B2

Reaction notes

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