Dimethyl Sulfoxide → HCID 58284935, compound

HRID 2279216Notes

Reaction equation

HRID 2279216 reaction equation
C([O-])([O-])=O.[K+].[K+].F[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15].C[O:18][C:19]([CH2:21][CH:22]1[NH:27][CH2:26][CH2:25][N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:23]1)=[O:20].CS(C)=O>O.Cl>[C:31]([O:30][C:28]([N:24]1[CH2:25][CH2:26][N:27]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])[CH:22]([CH2:21][C:19]([OH:20])=[O:18])[CH2:23]1)=[O:29])([CH3:34])([CH3:32])[CH3:33]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzene2×HCID 2756816Methyl 4-Boc-piperazine-2-acetate

Product 1

HCID 58284935HCID 58284935, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Solid K2CO3 (1070 mg, 7.74 mmol) was added to a mixture of 1-fluoro-2-nitrobenzene (655 mg, 4.65 mmol) and the product of Example 22B (1000 mg, 3.87 mmol). Dimethyl sulfoxide (40 mL) was added, and the mixture was heated at 100° C. with stirring under nitrogen. After 22 hours, additional 1-fluoro-2-nitrobenzene (350 mg) was added and heating was continued for 14 hours longer. The mixture was cooled to 40° C., diluted with water (400 mL), and aqueous 10% HCl (25 mL) was added to bring the pH˜3-4. The mixture was extracted with CHCl3 (4×200 mL). The combined extract was concentrated under vacuum to a residue that was purified by chromatography (SiO2, eluted with hexanes-ethyl acetate, 100:0-50:50-0:100) to provide the title compound: 1H NMR (300 MHz, CDCl3) δ ppm 1.48 (s, 9H), 2.34-2.55 (m, 1H), 2.73-2.90 (m, 1H), 3.20-3.42 (m, 2H), 3.55-3.82 (m, 4H), 3.93-4.12 (m, 1H), 7.13-7.23 (m, 2H), 7.45-7.55 (m, 1H), 7.74 (dd, J=7.9, 1.6 Hz, 1H).

Workup

  1. temperatureheating
  2. waitwas continued for 14 hours
  3. temperatureThe mixture was cooled to 40° C.
  4. additionwas added
  5. extractionThe mixture was extracted with CHCl3 (4×200 mL)
  6. extractionThe combined extract
  7. concentrationwas concentrated under vacuum to a residue that
  8. customwas purified by chromatography (SiO2, eluted with hexanes-ethyl acetate, 100:0-50:50-0:100)

Sources & evidence

ORD record
ord-bc3bc4d4d299434ebfc556e084a9f4a4
Source dataset
uspto-grants-2015_09
Patent number
US09133206B2

Reaction notes

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