Diisopropylethylamine → HCID 22273295, compound

HRID 1064581Notes

Reaction equation

HRID 1064581 reaction equation
[C:1]1([S:7]([N:10]2[CH:15]3[CH2:16][CH2:17][CH:11]2[CH2:12][N:13]([CH2:18][C:19](O)=[O:20])[CH2:14]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[C:23]1([CH3:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:24]1[NH2:25].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.[F:48][P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C)C=O>[F:48][C:29]1[C:23]([CH3:30])=[C:24]([NH:25][C:19](=[O:20])[CH2:18][N:13]2[CH2:12][CH:11]3[N:10]([S:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)(=[O:8])=[O:9])[CH:15]([CH2:16][CH2:17]3)[CH2:14]2)[CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 22273309HCID 22273309, compoundHCID 22273399HCID 22273399, compound

Product 1

HCID 22273295HCID 22273295, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the product of step (iii) (0.45 mmol), 2-fluoro-2-methylaniline (60 μl), PyBroP (0.25 g), N,N-dimethylaminopyridine (54 mg) and N,N-diisopropylethylamine (0.23 ml) in N,N-dimethylformamide (5 ml) was stirred at ambient temperature for 16 hours. The reaction mixture was partitioned between ethyl acetate and water. The organic phase was washed with water and brine, dried (MgSO4) and evaporated. The residue was purified by flash chromatography eluting with 1% ethanol in dichloromethane followed by further chromatography with 20% ethyl acetate/iso-hexane to give the title compound as a white solid. Yield: 30 mg.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by flash chromatography
  6. washeluting with 1% ethanol in dichloromethane

Sources & evidence

ORD record
ord-98b8a0b31768434c8fe6a2562b1a6270
Source dataset
uspto-grants-2005_11
Patent number
US06969713B2

Reaction notes

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