Diisopropylethylamine → HCID 35326857, compound

HRID 1942814Notes

Reaction equation

HRID 1942814 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH2:11])=[CH:6][CH:5]=1.CCN(C(C)C)C(C)C.[CH3:22][N:23]([CH3:28])[S:24](Cl)(=[O:26])=[O:25]>ClCCl.CN(C1C=CN=CC=1)C>[CH3:22][N:23]([CH3:28])[S:24]([NH:11][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([O:2][CH3:1])=[O:12])=[CH:5][CH:6]=1)(=[O:26])=[O:25]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 571728Methyl 4-(aminomethyl)benzoate

Product 1

HCID 35326857HCID 35326857, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

4-(aminomethyl)benzoic acid methyl ester (0.2676 g, 1.620 mmol) was dissolved in dichloromethane (15 ml). DMAP (0.0248 g, 0.203 mmol) and DIEA (0.35 ml, 2.004 mmol) were added. The solution was cooled to 0° C. Dimethylsulfamoyl chloride (0.18 ml, 1.676 mmol) was added. The reaction was allowed to stir until completion. The reaction was diluted with DCM and washed with aqueous sodium hydrogen carbonate. The aqueous layer was extracted with DCM two times. The combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography on silica gel, eluting with EtOAc/hexane (6-50%). MS: cal'd 273 (MH+), exp 273 (MH+).

Workup

  1. washwashed with aqueous sodium hydrogen carbonate
  2. extractionThe aqueous layer was extracted with DCM two times
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluting with EtOAc/hexane (6-50%)

Sources & evidence

ORD record
ord-b1f64ef496564448b0789be3e20b6d7a
Source dataset
uspto-grants-2013_03
Patent number
US08389553B2

Reaction notes

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