Diisopropylethylamine → HCID 17946656, compound

HRID 49723Notes

Reaction equation

HRID 49723 reaction equation
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[NH2:25][C:26]1[CH:27]=[CH:28][C:29]([CH:32]([CH3:39])[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[N:30][CH:31]=1.C(N(C(C)C)CC)(C)C.[C:49]([O:52][C:53]1[CH:54]=[C:55]([CH2:62][C:63](O)=[O:64])[CH:56]=[CH:57][C:58]=1[N+:59]([O-:61])=[O:60])(=[O:51])[CH3:50]>CN(C)C=O>[C:49]([O:52][C:53]1[CH:54]=[C:55]([CH2:62][C:63]([NH:25][C:26]2[CH:27]=[CH:28][C:29]([CH:32]([CH3:39])[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[N:30][CH:31]=2)=[O:64])[CH:56]=[CH:57][C:58]=1[N+:59]([O-:61])=[O:60])(=[O:51])[CH3:50]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 17946639(3-Acetoxy-4-nitro-phenyl)acetic acidHCID 17946645ethyl (3RS)-3-(5-aminopyrid-2-yl)butyrate

Product 1

HCID 17946656HCID 17946656, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
30 °C

Procedure

A solution of O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (10.95 g) in dry dimethylformamide (20 mL) was added to a solution of (RS) ethyl 3-(5-aminopyrid-2-yl)butanoate (3.0 g, Reference Example 5), diisopropylethylamine (10 mL) and (3-acetoxy-4-nitro-phenyl)acetic acid (6.89 g, Reference Example 17) in dimethylformamide (90 mL) under a nitrogen atmosphere. After stirring at 30° C. for 24 hours the reaction mixture was evaporated and the residue was partitioned between ethyl acetate and 5% aqueous sodium bicarbonate. The organic phase was washed with water, then with brine, then dried over magnesium sulphate, then treated with decolourising charcoal followed by filtration and evaporation of the filtrate to give the title compound as a dark oil.

Workup

  1. customwas evaporated
  2. customthe residue was partitioned between ethyl acetate and 5% aqueous sodium bicarbonate
  3. washThe organic phase was washed with water
  4. dry with materialwith brine, then dried over magnesium sulphate
  5. additiontreated with decolourising charcoal
  6. filtrationfollowed by filtration and evaporation of the filtrate

Sources & evidence

ORD record
ord-9ba64a1116f449bb9ec1ca7dc4da51be
Source dataset
uspto-grants-2004_03
Patent number
US06706738B2

Reaction notes

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