Hydrochloric Acid → HCID 67241116, compound

HRID 2422940Notes

Reaction equation

HRID 2422940 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[OH:15][C:16]1[CH:25]=[C:24]([NH:26][C:27](=[O:40])[CH:28]=[CH:29][C:30]2[CH:39]=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]=2)[CH:23]=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19].C1CCN2C(=NCCC2)CC1.Cl.[N+:53]([CH3:56])([O-:55])=[O:54]>CN(C=O)C.O>[CH2:1]([O:15][C:16]1[CH:25]=[C:24]([NH:26][C:27](=[O:40])[CH2:28][CH:29]([C:30]2[CH:39]=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]=2)[CH2:56][N+:53]([O-:55])=[O:54])[CH:23]=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 67242123HCID 67242123, compound

Product 1

HCID 67241116HCID 67241116, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Benzyl bromide (0.236 g, 1.38 mmol) and K2CO3 (0.190 g, 1.38 mmol) were added to a stirred solution of 43 (0.400 g, 1.15 mmol) in anhydrous DMF (7 ml) under Ar. The reaction mixture was stirred at room temperature overnight and the mixture was poured in water (15 ml). The product was extracted with ethyl acetate (2×15 ml), dried over Na2SO4 and the solvent removed under reduced pressure. The resultant product 44 was stirred in the microwave reactor in presence of DBU (0.192 g, 1.27 mmol), and nitromethane (7 ml) in the microwave), at 100° C. for 15 min. After cooling to room temperature, the reaction mixture was poured into HCl 1M (10 ml). The product was extracted with ethyl acetate (2×15 ml), dried over Na2SO4 and the solvent removed under reduced pressure. Chromatography on silica gel (60:40 hexanes/ethyl acetate) afforded 49 (0.413 g, 0.83 mmol, 72%) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 2.88 (1H, dd, J 6.8, 15.6 Hz), 2.96 (1H, dd, J 7.2, 15.2 Hz), 3.86 (3H, s), 4.26 (1H, quint, J 7.1 Hz), 4.83 (1H, dd, J 7.4, 12.6 Hz), 4.93 (1H, dd, J 6.8, 12.4 Hz), 5.10 (2H, s), 6.71 (1H, dd, J 2.0, 8.8 Hz), 7.13 (1H, bs), 7.28-7.32 (1H, m), 7.36-7.39 (3H, m), 7.47-7.52 (5H, m), 7.71 (1H, bs), 7.77-7.86 (4H, m). 13C NMR (400 MHz, CDCl3) δ 40.68, 40.81, 52.15, 70.70, 79.44, 101.39, 111.15, 115.91, 124.94, 126.67, 126.79, 126.89, 127.22, 127.93, 128.05, 128.79, 128.72, 129.39, 133.11, 133.60, 135.89, 136.54, 142.68, 159.61, 166.42, 168.57. MS (API-ES): m/z found 499 [M+H]+ (100%), HRMS (API-ES) m/z 499.1862 [M+H]+.

Workup

  1. extractionThe product was extracted with ethyl acetate (2×15 ml)
  2. dry with materialdried over Na2SO4
  3. customthe solvent removed under reduced pressure
  4. temperatureAfter cooling to room temperature
  5. extractionThe product was extracted with ethyl acetate (2×15 ml)
  6. dry with materialdried over Na2SO4
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-3fd397ade0cb462ebae21ce4ae43e37b
Source dataset
uspto-grants-2011_06
Patent number
US07960434B2

Reaction notes

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