Myristyl bromide → HCID 69331409, compound

HRID 1182210Notes

Reaction equation

HRID 1182210 reaction equation
[H-].[Na+].[C:3]1([NH:9][C:10]2[S:14][N:13]=[N:12][C:11]=2[C:15]([NH2:17])=[O:16])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].[K+].[Br-]>CN(C=O)C>[C:24]1([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:3][NH:9][C:10]2[S:14][N:13]=[N:12][C:11]=2[C:15]([NH2:17])=[O:16])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 8208Myristyl bromideHCID 24758Sodium hydrideHCID 253877Potassium BromideHCID 5148325HCID 5148325, compound

Product 1

HCID 69331409HCID 69331409, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice-cooled suspension of NaH (19 mg, 60 wt % in oil, 0.46 mmole) in 3 mL of DMF was added 5-phenylamino-[1,2,3]thiadiazole-4-carboxylic acid amide (100 mg, 0.46 mmole). The mixture was stirred at room temperature for 1 h. 1-Bromotetradecane (131 mg, 0.47 mmole) was then added to the reaction mixture which was cooled in an ice bath. The reaction was carried out overnight with stirring and then quenched with a mixture of 5 mL of saturated aqueous NH4Cl, 5 mL of saturated aqueous NaCl and 10 mL EtOAc. The aqueous layer was extracted with EtOAc (2×10 mL). The combined organic layers were dried with anhydrous Na2SO4, concentrated and then purified by preparative TLC with hexane:EtOAc (1:1) as the eluant. A white powder product was obtained (122 mg, 66%). m.p. 79-81° C. 1H NMR (ppm, CDCl3): 7.60-7.44 (m, 5H), 7.20 (s, br., 1H), 5.63 (s, br., 1H), 2.96 (t, 2H), 1.43-1.00 (m, 24H), 0.88 (t, 3H). FTIR (cm−1, KBr pellet): 3386, 3299, 2918, 2851, 1674, 1657, 1600, 1527, 1503, 1384, 1299, 999, 766, 743, 693.

Workup

  1. temperaturewas cooled in an ice bath
  2. waitThe reaction was carried out overnight
  3. stirringwith stirring
  4. customquenched with a mixture of 5 mL of saturated aqueous NH4Cl, 5 mL of saturated aqueous NaCl and 10 mL EtOAc
  5. extractionThe aqueous layer was extracted with EtOAc (2×10 mL)
  6. dry with materialThe combined organic layers were dried with anhydrous Na2SO4
  7. concentrationconcentrated
  8. custompurified by preparative TLC with hexane:EtOAc (1:1) as the eluant
  9. customA white powder product was obtained (122 mg, 66%)

Sources & evidence

ORD record
ord-d703e638a89147859e01d2e8744daba9
Source dataset
uspto-grants-2007_10
Patent number
US07288556B2

Reaction notes

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