Diisopropylethylamine → HCID 28973468, compound

HRID 929108Notes

Reaction equation

HRID 929108 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][NH2:10])(C)(C)C.CCN(C(C)C)C(C)C.[Br:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[S:28](Cl)(=[O:30])=[O:29]>C(Cl)Cl>[NH2:10][CH2:9][CH2:8][NH:7][S:28]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[Br:21])(=[O:30])=[O:29]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 187201N-BOC-ethylenediamineHCID 5204032-Bromobenzenesulfonyl chloride

Product 1

HCID 28973468HCID 28973468, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To solution of (2-amino-ethyl)-carbamic acid tert-butyl ester (208 mg, 1.3 mmol) in CH2Cl2 (20 mL) was added DIEA (300 μL, 1.72 mmol) at 0° C., followed by the addition of 2-bromo-benzenesulfonyl chloride (383 mg, 1.5 mmol). After it was stirred at 0° C. for 1 h and at the room temperature for another 16 h, the reaction mixture was evaporated thoroughly. The residue was diluted with 20% TFA in CH2Cl2 (10 mL), stirred for 3 h at the room temperature, and evaporated. Chromatography of the residual crude with CH2Cl2/MeOH/28% aqueous NH4OH (90:10:1) afforded the title compound (313 mg, 86%). 1H NMR (DMSO-d6) δ 2.86 (t, J=8 Hz, 2H), 3.04 (t, J=8 Hz, 2H), 7.55-7.65 (2H), 7.89 (d, J=8 Hz, 1H), 8.01 (d, J=8 Hz, 1H); ESI-MS m/z 279.1 (MH+).

Workup

  1. customthe reaction mixture was evaporated thoroughly
  2. additionThe residue was diluted with 20% TFA in CH2Cl2 (10 mL)
  3. stirringstirred for 3 h at the room temperature
  4. customevaporated

Sources & evidence

ORD record
ord-a92f84f84aec46a59382d2c1d8d32d7b
Source dataset
uspto-grants-2016_03
Patent number
US09290503B2

Reaction notes

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