Triethylamine → HCID 18506825, compound

HRID 1355485Notes

Reaction equation

HRID 1355485 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:9](Cl)(Cl)=[S:10].C(N(CC)CC)C.[CH3:20][O:21][C:22]([O:31][CH3:32])([C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1)[CH2:23][NH2:24]>C(Cl)Cl>[CH3:20][O:21][C:22]([O:31][CH3:32])([C:25]1[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=1)[CH2:23][NH:24][C:9]([NH:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1)=[S:10]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 153472-Amino-3-methylpyridineHCID 10442338HCID 10442338, compound

Product 1

HCID 18506825HCID 18506825, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

2-Amino-3-methylpyridine (19-1, 0.281 g, 2.60 mmol) was stirred in 6 mL anhydrous DCM under N2. Thiophosgene (0.198 mL, 2.60 mmol) was added followed by the addition of triethylamine (1.09 mL, 7.79 mmol) and an additional 4 mL anhydrous DCM. After 30 min 2,2-dimethoxy-2-pyridin-4-yl-ethylamine (0.430 g, 2.36 mmol, Ganellin, C. R.; Hosseini, S. K.; Khalaf, Y. S.; Tertiuk, W.; Arrang, J.-M.; et al. J.Med.Chem. 1995, 38, 3342-3350) was added as a solution in 2 mL anhydrous DCM. After 16 h the reaction was quenched with sat NaHCO3 (aq) and extracted 3× with DCM. The combined organic extracts were dried over Na2SO4, filtered, and concentrated to provide the pure titled compound as a tan solid. 1H NMR (CDCl3) δ11.88 (s, 1H), 8.65 (d, 2H, J=6.0 Hz), 7.76 (m, 2H), 7.50 (d, 2H, J=6.2 Hz), 7.44 (m, 1H), 6.87 (dd, 1H, J=5.1, 7.3 Hz), 4.22 (d, 2H, J=5.0 Hz), 3.29 (s, 6H), 2.22 (s, 3H).

Workup

  1. customAfter 16 h the reaction was quenched with sat NaHCO3 (aq)
  2. extractionextracted 3× with DCM
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0634e247f31c40698a68b6c954d3d336
Source dataset
uspto-grants-2003_07
Patent number
US06586423B2

Reaction notes

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