Diisopropylethylamine → HCID 86723239, compound

HRID 1846016Notes

Reaction equation

HRID 1846016 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4](O)=[O:5].C[N:18](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([NH2:18])=[O:5]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 43140622HCID 43140622, compound

Product 1

HCID 86723239HCID 86723239, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromo-5-(isopropylsulfonyl)benzoic acid (Preparation 23, 623 mg, 2.03 mmol) and HATU (925 mg, 2.44 mmol) were dissolved in DMF (10 mL) and diisopropylethylamine (1.74 mL, 10.0 mmol) was added dropwise to the mixture. The mixture was stirred for 1 hour and then partitioned between water (50 mL) and EtOAc (25 mL). The aqueous layer was extracted with EtOAc (2×10 mL) and the combined organic extracts were washed with saturated brine (20 mL) and dried (MgSO4). The solvent was removed under reduced pressure to leave a pale yellow solid. This material was purified by silica gel column chromatography eluting with MeOH/CH2Cl2 3:97 to give the title compound as a white solid 59% yield, 362 mg.

Workup

  1. custompartitioned between water (50 mL) and EtOAc (25 mL)
  2. extractionThe aqueous layer was extracted with EtOAc (2×10 mL)
  3. washthe combined organic extracts were washed with saturated brine (20 mL)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed under reduced pressure
  6. customto leave a pale yellow solid
  7. customThis material was purified by silica gel column chromatography
  8. washeluting with MeOH/CH2Cl2 3:97

Sources & evidence

ORD record
ord-bc72f7440da549bdbdcbefd10046fd19
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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