Triethylamine → HCID 86270912, compound

HRID 2177587Notes

Reaction equation

HRID 2177587 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:15]2[CH2:14][CH2:13][NH:12][CH2:11][C:10]=2[N:9]=[N:8]1.[Cl:16][C:17]1[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:23]=[CH:22][C:18]=1[C:19](Cl)=[O:20].CCN(CC)CC>C1COCC1.C(Cl)Cl>[Cl:16][C:17]1[C:25]([C:26]([F:28])([F:29])[F:27])=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([N:12]1[CH2:13][CH2:14][C:15]2[N:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[N:8]=[N:9][C:10]=2[CH2:11]1)=[O:20]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 38276332-Chloro-3-(trifluoromethyl)benzoyl chlorideHCID 90409239HCID 90409239, compound

Product 1

HCID 86270912HCID 86270912, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(pyridin-2-yl)-4,5,6,7-tetrahydro-1H-[1,2,3]triazolo[4,5-c]pyridine (13 mg, 0.065 mmol) in THF (1 mL) was treated with 2-chloro-3-(trifluoromethyl)benzoyl chloride (19 mg, 0.078 mmol) followed by Et3N (0.013 mL, 0.097 mmol). After 5 min the reaction was diluted with CH2Cl2 and the organic portion washed with NaHCO3. The organic portion was then dried over Na2SO4, concentrated and purified on 4 g SiO2 to yield 20 mg (75%) of: 5-{[2-Chloro-3-(trifluoromethyl)phenyl]carbonyl}-1-pyridin-2-yl-4,5,6,7-tetrahydro-1H-[1,2,3]triazolo[4,5-c]pyridine. MS (ESI): mass calcd. for C18H13ClF3N5O, 407.1. m/z found, 408.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.49 (dddd, J=32.1, 4.9, 1.8, 0.8 Hz, 1H), 8.17 (ddt, J=17.3, 8.3, 1.0 Hz, 1H), 7.93 (ddt, J=8.4, 7.5, 1.7 Hz, 1H), 7.79 (ddd, J=6.6, 4.4, 2.2 Hz, 1H), 7.57-7.42 (m, 2H), 7.35 (dddd, J=12.3, 7.5, 4.9, 1.0 Hz, 1H), 5.25-4.96 (m, 1H), 4.35 (dt, J=13.3, 5.4 Hz, 1H), 4.11-3.95 (m, 1H), 3.61-3.53 (m, 1H), 3.51-3.44 (m, 1H), 3.36 (s, 1H).

Workup

  1. washthe organic portion washed with NaHCO3
  2. dry with materialThe organic portion was then dried over Na2SO4
  3. concentrationconcentrated
  4. custompurified on 4 g SiO2

Sources & evidence

ORD record
ord-d79ce725eb624365910401aca6e15b22
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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