Dimethylformamide → HCID 58182722, compound

HRID 2191547Notes

Reaction equation

HRID 2191547 reaction equation
[Br:1][C:2]1[N:6]=[C:5](Cl)[S:4][N:3]=1.[NH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:21])[O:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:10][CH2:9]1.CN(C=O)C>O>[Br:1][C:2]1[N:6]=[C:5]([N:8]2[CH2:9][CH2:10][CH:11]([NH:14][C:15](=[O:21])[O:16][CH2:17][CH:18]([CH3:19])[CH3:20])[CH2:12][CH2:13]2)[S:4][N:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 27250533-Bromo-5-chloro-1,2,4-thiadiazoleHCID 15676964Isobutyl piperidin-4-ylcarbamate

Product 1

HCID 58182722HCID 58182722, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-bromo-5-chloro-1,2,4-thiadiazole (0.21 g, 1.1 mmol), isobutyl piperidin-4-ylcarbamate (0.23 g, 1.2 mmol), and DMF (2 mL) was sealed in a microwave vessel and heated by microwave irradiation at 100° C. for two minutes. The reaction was cooled to room temperature, diluted with water, and extracted with CH2Cl2. The combined extracts were washed with water, dried over Na2SO4, and concentrated under reduced pressure to yield isobutyl 1-(3-bromo-1,2,4-thiadiazol-5-yl)piperidin-4-ylcarbamate. LC/MS: m/z 365.0 (M+H)+ at 3.20 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customwas sealed in a microwave vessel
  2. temperatureThe reaction was cooled to room temperature
  3. extractionextracted with CH2Cl2
  4. washThe combined extracts were washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9530f545dde54a1b883ee0468a89a5df
Source dataset
uspto-grants-2012_12
Patent number
US08329702B2

Reaction notes

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