Triethylamine → HCID 86271494, compound

HRID 2177637Notes

Reaction equation

HRID 2177637 reaction equation
[Cl-].[F:2][C:3]1[CH:4]=[N:5][C:6]([NH+:9]2[C:17]3[CH2:16][C@H:15]([CH3:18])[NH:14][CH2:13][C:12]=3[N:11]=[N:10]2)=[N:7][CH:8]=1.C(N(CC)CC)C.[F:26][C:27]1[C:35]([C:36]([F:39])([F:38])[F:37])=[CH:34][CH:33]=[CH:32][C:28]=1[C:29](Cl)=[O:30].C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:2][C:3]1[CH:4]=[N:5][C:6]([N:9]2[C:17]3[CH2:16][C@H:15]([CH3:18])[N:14]([C:29]([C:28]4[CH:32]=[CH:33][CH:34]=[C:35]([C:36]([F:37])([F:38])[F:39])[C:27]=4[F:26])=[O:30])[CH2:13][C:12]=3[N:11]=[N:10]2)=[N:7][CH:8]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 27375592-Fluoro-3-(trifluoromethyl)benzoyl chlorideHCID 178461165HCID 178461165, compound

Product 1

HCID 86271494HCID 86271494, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-1-(5-fluoropyrimidin-2-yl)-6-methyl-4,5,6,7-tetrahydro-1H-[1,2,3]triazolo[4,5-c]pyridinium chloride (0.575 g, 2.12 mmol) in CH2Cl2 (10 mL) was added triethylamine (1.18 mL, 8.50 mmol) followed by 2-fluoro-3-(trifluoromethyl)benzoyl chloride (0.625 g, 2.76 mmol). After stirring for 30 min at rt, sat NaHCO3 (20 mL) was added. The organic layer was separated and the water layer was extracted with CH2Cl2 two times. The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated. Chromatography on silica gel (0-100% ethyl acetatehexanes) provided the desired product as a white solid (0.837 g, 93%). MS (ESI) mass calcd. C18H13F5N6O, 424.11. m/z found, 425.1 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 8.75 (s, 2H), 7.81-7.49 (m, 2H), 7.46-7.30 (m, 1H), 5.92-5.66 (m, 0.5H), 5.68-5.55 (m, 0.5H), 4.81-4.54 (m, 1H), 4.37 (d, J=16.9 Hz, 0.5H), 4.30-4.18 (m, 0.5H), 3.58-3.40 (m, 0.8H), 3.34-3.12 (m, 1.2H), 1.43-1.12 (m, 3H).

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. extractionthe water layer was extracted with CH2Cl2 two times
  4. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8569bb69e41e41cbb101692ba468143b
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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