Triethylamine → HCID 59176612, compound

HRID 628683Notes

Reaction equation

HRID 628683 reaction equation
Cl.Cl.Cl.Cl.[NH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH:17]=[C:16]([CH2:18][N:19]([CH3:30])[CH:20]2[C:29]3[N:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH2:23][CH2:22][CH2:21]2)[N:15]=[N:14]1.[N:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH:37]=O.C(N(CC)CC)C.[BH4-].[Na+]>CO.[Cl-].[Na+].O>[CH3:30][N:19]([CH2:18][C:16]1[N:15]=[N:14][N:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][NH:5][CH2:37][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][N:31]=2)[CH:17]=1)[CH:20]1[C:29]2[N:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH2:23][CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 142732-PyridinecarboxaldehydeHCID 4311764Sodium borohydrideHCID 68794390HCID 68794390, compound

Product 1

HCID 59176612HCID 59176612, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-((1-(2-(aminomethyl)phenyl)-1H-1,2,3-triazol-4-yl)methyl)-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine tetrahydrochloride, AD, (0.20 g, 0.43 mmol) in methanol (2 mL) was added 2-pyridine carboxaldehyde (0.04 mL, 0.43 mmol) and triethylamine (0.18 mL, 1.30 mmol). The reaction mixture was heated to 60° C. and stirred for 18 h. The reaction mixture was then cooled to room temperature and NaBH4 (0.05 g, 1.30 mmol) was added. The reaction stirred 1 h at room temperature. The reaction mixture was poured into brine (10 mL) and was extracted with ethyl acetate (2×10 mL). The combined organic phases were dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by chromatography on basic alumina (0-5% methanol/dichloromethane) yielding AG. ESI+ MS: m/z (rel intensity) 440 (100, M+H).

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. stirringThe reaction stirred 1 h at room temperature
  3. extractionwas extracted with ethyl acetate (2×10 mL)
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by chromatography on basic alumina (0-5% methanol/dichloromethane)
  8. customyielding AG

Sources & evidence

ORD record
ord-7f5e0522e2fa45c88e1295ad6972c8f5
Source dataset
uspto-grants-2016_04
Patent number
US09314468B2

Reaction notes

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