Diisopropylethylamine → HCID 70233351, compound

HRID 1887432Notes

Reaction equation

HRID 1887432 reaction equation
C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[NH2:34][C:35]1[CH:36]=[C:37]2[C:44]3([CH2:49][CH2:48][S:47][C:46]([NH:50][C:51](=[O:57])[O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[N:45]3)[CH2:43][CH2:42][O:41][C:38]2=[CH:39][CH:40]=1.C(N(CC)C(C)C)(C)C.[C:67]([C:69]1[CH:70]=[CH:71][C:72]([C:75](O)=[O:76])=[N:73][CH:74]=1)#[N:68].C(=O)(O)[O-].[Na+]>ClCCl>[C:67]([C:69]1[CH:70]=[CH:71][C:72]([C:75]([NH:34][C:35]2[CH:36]=[C:37]3[C:44]4([CH2:49][CH2:48][S:47][C:46]([NH:50][C:51](=[O:57])[O:52][C:53]([CH3:54])([CH3:56])[CH3:55])=[N:45]4)[CH2:43][CH2:42][O:41][C:38]3=[CH:39][CH:40]=2)=[O:76])=[N:73][CH:74]=1)#[N:68]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2724699PyBOPHCID 124007345-Cyanopyridine-2-carboxylic acid2×HCID 58316538HCID 58316538, compound

Product 1

HCID 70233351HCID 70233351, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

PyBOP (74.5 mg) was added to a solution of the compound 10 obtained in Example 3 (25.0 mg), N,N-diisopropylethylamine (0.0624 ml) and 5-cyanopyridine-2-carboxylic acid (Compound 9-3) (16.9 mg) in dichloromethane (5.0 ml) at room temperature. The mixture was stirred at room temperature for one hour. The reaction solution was poured into aqueous sodium bicarbonate, followed by extraction with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to obtain the title compound (35 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe drying agent was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-30ea1edd166740c9bcf8cbc90d45453c
Source dataset
uspto-grants-2013_08
Patent number
US08501733B2

Reaction notes

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