Triethylamine → HCID 23449993, compound

HRID 1838926Notes

Reaction equation

HRID 1838926 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.[F:18][C:19]1[C:27]([O:28][CH3:29])=[CH:26][CH:25]=[CH:24][C:20]=1C(O)=O.C([N:32]([CH2:35]C)CC)C.[F:37][C:38]1[CH:45]=[CH:44][CH:43]=[C:42]([F:46])[C:39]=1[CH2:40][NH2:41]>C1(C)C=CC=CC=1.BrC1C=CC=CC=1.ClCCl>[F:18][C:19]1[C:27]([O:28][CH3:29])=[CH:26][CH:25]=[CH:24][C:20]=1[NH:32][C:35]([NH:41][CH2:40][C:39]1[C:38]([F:37])=[CH:45][CH:44]=[CH:43][C:42]=1[F:46])=[O:8]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 1235632,6-DifluorobenzylamineHCID 199401P,P-Diphenylphosphinic azideHCID 33906792-Fluoro-3-methoxybenzoic acid

Product 1

HCID 23449993HCID 23449993, compoundYield 76.1%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 7961BromobenzeneSolvent

Procedure

A solution of diphenylphosphoryl azide (3.19 g, 2.50 mL, 11.6 mmol) in toluene (3 mL) was added dropwise to a solution of 2-fluoro-3-methoxybenzoic acid (1.70 g, 10 mmol) and triethylamine (1.17 g, 1.62 mL, 11.6 mmol) in anhydrous bromobenzene (20 mL). The reaction mixture was stirred at room temperature for 30 minutes and heated at 95° C. for 20 minutes. The reaction was cooled to ambient temperature and a solution of 2,6-difluorobenzylamine (1.43 g, 10 mmol) in dichloromethane (5 mL) was added. The mixture was stirred at ambient temperature for half of an hour, filtered, and washed with dichloromethane and ether to give a white solid (2.36 g, 76.1%). 1H NMR (DMSO-d6) δ3.77 (s, 3H), 4.35 (d, J=5.4 Hz, 2H), 6.69-7.70 (m, 6H), 7.07 (br s, 1H), 8.29 (br s, 1H); MS (CI) m/z 311.0 (MH+).

Workup

  1. temperatureheated at 95° C. for 20 minutes
  2. temperatureThe reaction was cooled to ambient temperature
  3. stirringThe mixture was stirred at ambient temperature for half of an hour
  4. filtrationfiltered
  5. washwashed with dichloromethane and ether

Sources & evidence

ORD record
ord-39666b6c38c943998a6467605ee3b9a3
Source dataset
uspto-grants-2004_01
Patent number
US06677340B2

Reaction notes

Loading…