Diisopropylethylamine → HCID 9864043, compound

HRID 2116448Notes

Reaction equation

HRID 2116448 reaction equation
Cl[C:2]1[N:10]=[C:9](S(CCC)(=O)=O)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1.[NH:24]1[CH2:31][CH2:30][CH2:29][C@H:25]1[C:26]([NH2:28])=[O:27].[CH:32]([N:35](CC)C(C)C)(C)C>O1CCCC1>[Cl:23][C:20]1[CH:19]=[CH:18][C:17]([N:6]2[CH:5]=[N:4][C:3]3[C:7]2=[N:8][C:9]([C:32]#[N:35])=[N:10][C:2]=3[N:24]2[CH2:31][CH2:30][CH2:29][C@H:25]2[C:26]([NH2:28])=[O:27])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 111306L-ProlinamideHCID 85908161HCID 85908161, compound

Product 1

HCID 9864043HCID 9864043, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

A solution of the product from step (iii) (0.2 g), L-prolinamide (0.062 g) and N,N-diisopropylethylamine (0.19 ml) in tetrahydrofuran (10 ml) was stirred at room temperature for 24 h. The solvent was removed, the residue dissolved in N,N-dimethylformamide (10 ml) and sodium cyanide (0.05 g) added and heated at 90° C. for 10 h. The mixture was partitioned between ethyl acetate and water, the organics dried (MgSO4) and evaporated under reduced pressure. The residue was purified by RPHPLC. Yield 0.062 g

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue dissolved in N,N-dimethylformamide (10 ml)
  3. additionsodium cyanide (0.05 g) added
  4. customThe mixture was partitioned between ethyl acetate and water
  5. dry with materialthe organics dried (MgSO4)
  6. customevaporated under reduced pressure
  7. customThe residue was purified by RPHPLC

Sources & evidence

ORD record
ord-552af0a54c404bacbbf114eed1eb6279
Source dataset
uspto-grants-2008_10
Patent number
US07439240B2

Reaction notes

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