Triethylamine → HCID 89705388, compound

HRID 928976Notes

Reaction equation

HRID 928976 reaction equation
[F:1][C:2]1[C:7]2[N:8]=[CH:9][O:10][C:6]=2[CH:5]=[C:4](C(O)=O)[C:3]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:16]=1[F:22].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])=CC=1.C([N:42]([CH2:45]C)CC)C>CC(O)(C)C>[F:1][C:2]1[C:7]2[N:8]=[CH:9][O:10][C:6]=2[CH:5]=[C:4]2[NH:42][C:45](=[O:30])[N:14]([C:15]3[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:16]=3[F:22])[C:3]=12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 89704789HCID 89704789, compound

Product 1

HCID 89705388HCID 89705388, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of 4-fluoro-5-((2-fluoro-4-iodophenyl)amino)benzo[d]oxazole-6-carboxylic acid (70 mg, 0.17 mmol) in t-BuOH (3 mL) was added DPPA (82 mg, 0.29 mmol) followed by triethylamine (36 mg, 0.36 mmol). The mixture was heated under reflux for 3 h and allowed to slowly warm to room temperature. The solvent was removed in vacuo and the resultant crude product was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 2:1, v/v). The corresponding product was obtained (white solid, 62 mg, 89.2% yield). 1H NMR (400 MHz, DMSO-d6): δ 11.75 (s, 1H), 8.67 (s, 1H), 7.96 (d, 1H), 7.76 (d, 1H), 7.50 (m, 1H), 7.39 (s, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 h
  3. customThe solvent was removed in vacuo
  4. customthe resultant crude product was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 2:1
  5. customThe corresponding product was obtained (white solid, 62 mg, 89.2% yield)

Sources & evidence

ORD record
ord-783a465b36c2458cafc99c023b97bd00
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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