Diisopropylethylamine → HCID 89782334, compound

HRID 1056434Notes

Reaction equation

HRID 1056434 reaction equation
[NH2:1][C:2]1[C:10]([Br:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.[CH3:13][S:14]([CH2:17][CH2:18][NH2:19])(=[O:16])=[O:15].CCN(C(C)C)C(C)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>CCOC(C)=O>[NH2:1][C:2]1[C:10]([Br:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:19][CH2:18][CH2:17][S:14]([CH3:13])(=[O:16])=[O:15])=[O:6]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 2702592-Amino-3-bromobenzoic acidHCID 17749886Ethanamine, 2-(methylsulfonyl)-, hydrochloride (1:1)

Product 1

HCID 89782334HCID 89782334, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 100-mL round-bottomed flask was added 2-amino-3-bromobenzoic acid (0.8 g, 3.70 mmol) and 2-(methylsulfonyl)ethanamine hydrochloride (0.709 g, 4.44 mmol, ChemBridge Inc.) in EtOAc (15 mL) followed by DIEA (1.61 mL, 9.26 mmol) and T3P (2.59 mL, 4.07 mmol, Sigma Aldrich). The mixture was stirred at RT for 2 h, then quenched with sat. NaHCO3. EtOAc (100 mL) was added and the layers were separated. The organic layer was washed with sat. NaHCO3 (20 mL), brine (15 mL), then dried (MgSO4), filtered and concentrated to give the crude product 485 mg. MS (ESI, pos. ion) m/z: 321 (M+1).

Workup

  1. customquenched with sat. NaHCO3
  2. additionEtOAc (100 mL) was added
  3. customthe layers were separated
  4. washThe organic layer was washed with sat. NaHCO3 (20 mL), brine (15 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2d440a97c36346c7b119e6e76336b648
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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