Hydrochloric Acid → HCID 51349356, compound

HRID 924897Notes

Reaction equation

HRID 924897 reaction equation
[CH2:1]([O:3][C:4]1[C:9]2[NH:10][C:11](=[O:13])[O:12][C:8]=2[CH:7]=[C:6]([CH:14]=O)[CH:5]=1)[CH3:2].[C:16]1([C:22](=O)[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[NH2:31][C:32]([NH2:34])=[O:33].Cl>C(O)C>[CH2:1]([O:3][C:4]1[C:9]2[NH:10][C:11](=[O:13])[O:12][C:8]=2[CH:7]=[C:6]([CH:14]2[C:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:22]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[NH:34][C:32](=[O:33])[NH:31]2)[CH:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 99482-PhenylacetophenoneHCID 58706352HCID 58706352, compound2×

Product 1

HCID 51349356HCID 51349356, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-ethoxy-2-oxo-2,3-dihydrobenzo[d]oxazole-6-carbaldehyde (Intermediate 76) (70 mg, 0.34 mmol), 1,2-diphenylethanone (70 mg, 0.36 mmol) and urea (82 mg, 1.4 mmol) in 5 mL of ethanol was added 0.2 ml con. HCl under N2. The reaction mixture was refluxed overnight. The reaction mixture was purified by prep-HPLC (0.1% TFA as additive) and solvent removed to give Compound 150 as white solid (32 mg, yield 22%). 1H NMR (CD3OD 400 MHz): 7.27 (m, 5H), 7.06-7.04 (m, 3H), 6.92-6.87 (m, 3H), 6.82 (s, 1H), 5.33 (s, 1H), 4.14-4.08 (m, 2H), 1.41 (t, J=6.8 Hz, 3H). MS (ESI): m/z 428.2 [M+1]+.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customThe reaction mixture was purified by prep-HPLC (0.1% TFA as additive) and solvent
  3. customremoved

Sources & evidence

ORD record
ord-bbb66f0402214fc8ad0d22e88f9f88b1
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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