Hydrochloric Acid → HCID 51347038, compound

HRID 401114Notes

Reaction equation

HRID 401114 reaction equation
[Si]([O:8][C:9]1[C:16]([CH2:17][CH2:18][CH3:19])=[CH:15][C:12]([CH:13]=O)=[CH:11][C:10]=1[N+:20]([O-:22])=[O:21])(C(C)(C)C)(C)C.[C:23]1([C:29](=O)[CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[NH2:38][C:39]([NH2:41])=[O:40].Cl>C(O)C>[OH:8][C:9]1[C:16]([CH2:17][CH2:18][CH3:19])=[CH:15][C:12]([CH:13]2[C:30]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[C:29]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[NH:41][C:39](=[O:40])[NH:38]2)=[CH:11][C:10]=1[N+:20]([O-:22])=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 99482-PhenylacetophenoneHCID 86669342HCID 86669342, compound2×

Product 1

HCID 51347038HCID 51347038, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(tert-butyldimethylsilyloxy)-3-nitro-5-propylbenzaldehyde (Intermediate 81) (100 mg, 0.31 mmol), 1,2-diphenylethanone (78 mg, 0.40 mmol) and urea (60 mg, 1.0 mmol) in ethanol (5 mL) was added conc. HCl (0.2 mL) and the reaction mixture was refluxed under N2 atmosphere overnight. Reaction was cooled and then purified by prep-HPLC (0.1% TFA as additive). The solution was concentrated under reduced pressure to give Compound 156 as a yellow solid (21 mg, yield 16%). 1H NMR (CD3OD 400 MHz): δ 7.95 (d, J=2.0 Hz, 1H), 7.52 (s, 1H), 7.26 (m, 5H), 7.06-7.03 (m, 3H), 6.89-6.86 (m, 2H), 5.39 (s, 1H), 2.70 (t, J=7.6 Hz, 2H), 1.66-1.59 (m, 2H), 0.93 (t, J=7.2 Hz, 3H). MS (ESI): m/z 430.2 [M+1]+.

Workup

  1. temperaturethe reaction mixture was refluxed under N2 atmosphere overnight
  2. customReaction
  3. temperaturewas cooled
  4. custompurified by prep-HPLC (0.1% TFA as additive)
  5. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a632aa2e0d864204992579f0ea24a8ca
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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