Hydrochloric Acid → HCID 51347038, compound

HRID 924903Notes

Reaction equation

HRID 924903 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-265cfc54a6d145f5b285e2d5e27519a6
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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