Diethylamine → HCID 11640425, compound

HRID 1454814Notes

Reaction equation

HRID 1454814 reaction equation
[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][C:4]([S:7]([NH:10][C:11]2[N:16]=[C:15]([CH2:17][C:18]([OH:20])=O)[CH:14]=[CH:13][CH:12]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH2:54]([NH:56][CH2:57][CH3:58])[CH3:55]>C(#N)C>[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][C:4]([S:7]([NH:10][C:11]2[N:16]=[C:15]([CH2:17][C:18]([N:56]([CH2:57][CH3:58])[CH2:54][CH3:55])=[O:20])[CH:14]=[CH:13][CH:12]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 23120833HCID 23120833, compound

Product 1

HCID 11640425HCID 11640425, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

[6-(Biphenyl-4-sulfonylamino)-pyridin-2-yl]-acetic acid (0.35 g) in acetonitrile (5 mL) was treated at RT with N,N-ethyldiisopropylamine (0.16 mL), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP, 0.252 g) then diethylamine (0.05 mL), and the mixture was stirred at RT for 16 h. It was then partitioned between cold diluted aqueous HCl and AcOEt, the layers were separated, the organic layer dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (heptane/EtOAc 1:1) to give 2-[6-(biphenyl-4-sulfonylamino)-pyridin-2-yl]-N,N-diethyl-acetamide as a yellow solid (0.168 g). MS (ESI−): 422.2 ([M−H]−).

Workup

  1. customIt was then partitioned between cold diluted aqueous HCl and AcOEt
  2. customthe layers were separated
  3. dry with materialthe organic layer dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography (heptane/EtOAc 1:1)

Sources & evidence

ORD record
ord-89b484dec394485cb6d438636d054e42
Source dataset
uspto-grants-2009_01
Patent number
US07482341B2

Reaction notes

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