1,4-Dibromobutane → HCID 21906373, compound

HRID 1882994Notes

Reaction equation

HRID 1882994 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([NH:10][C:11]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:12]=2[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=2)=[O:14])=[O:9])[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:35][CH2:36][CH2:37][CH2:38]Br>CN(C)C=O.C(OCC)(=O)C>[ClH:22].[Cl:27][C:24]1[CH:25]=[CH:26][C:11]([NH:10][C:8]([CH:5]2[CH2:6][CH2:7][CH:2]([N:1]3[CH2:38][CH2:37][CH2:36][CH2:35]3)[CH2:3][CH2:4]2)=[O:9])=[C:12]([CH:23]=1)[C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=1)=[O:14]

Participants

6

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 21906165HCID 21906165, compound

Product 1

HCID 21906373HCID 21906373, compoundYield 154.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

2-[(4-Aminocyclohexylcarbonyl)amino)-5-chloro-N-(5-chloropyridin-2-yl)benzamide (300 mg, 0.74 mmol) was diluted with dimethylformamide (8 mL). Potassium carbonate (307 mg, 2.22 mmol) and 1,4-dibromobutane (88 mL, 0.74 mmol) were added. The reaction was heated to 80° C. over the weekend. The reaction was cooled to room temperature, diluted with ethyl acetate (50 mL) and washed with water (5×10 mL). The ethyl acetate layer was dried over sodium sulfate, filtered and concentrated. The crude material was purified by HPLC to give 284 mg (77%) of the title compound as a white solid.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. washwashed with water (5×10 mL)
  3. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by HPLC

Sources & evidence

ORD record
ord-ce14e68eabfa42e6af46db6cd66140c9
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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