Triethylamine → HCID 66776729, compound

HRID 1616099Notes

Reaction equation

HRID 1616099 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6](Cl)=[O:7])([O-:3])=[O:2].[F:13][C:14]([F:25])([F:24])[CH2:15][S:16][C:17]1[N:22]=[C:21]([NH2:23])[CH:20]=[CH:19][N:18]=1.C(N(CC)CC)C>C(Cl)Cl>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([NH:23][C:21]1[CH:20]=[CH:19][N:18]=[C:17]([S:16][CH2:15][C:14]([F:25])([F:24])[F:13])[N:22]=1)=[O:7])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 118752-Nitrobenzoyl chlorideHCID 66776385HCID 66776385, compound

Product 1

HCID 66776729HCID 66776729, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-nitrobenzoyl chloride (1.85 g, 10 mmol) in CH2Cl2 (10 mL) was slowly added to a solution of 2-(2,2,2-trifluoro-ethylsulfanyl)-pyrimidin-4-ylamine (2.1 g, 10 mmol) and triethylamine (2 g, 20 mmol) in CH2Cl2 (80 mL) between 0 and max 7° C. The mixture was stirred overnight at room temperature and then poured into ice-water. The phases were separated and the organic part was dried with Na2SO4, filtered and concentrated in vacuo to provide a viscous oil. The crude product was purified by prep-HPLC (1.5 g, 41.8%).

Workup

  1. customThe phases were separated
  2. dry with materialthe organic part was dried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto provide a viscous oil
  6. customThe crude product was purified by prep-HPLC (1.5 g, 41.8%)

Sources & evidence

ORD record
ord-7e0973234de84ee898b8494633401f01
Source dataset
uspto-grants-2014_07
Patent number
US08765774B2

Reaction notes

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