Nicotinic Acid → HCID 11442085, compound

HRID 1986358Notes

Reaction equation

HRID 1986358 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:31][C:32]1[CH:33]=[C:34]([O:38][C:39]2[N:44]=[CH:43][C:42]3[N:45]=[C:46]([C:50]4[C:51]([NH2:55])=[N:52][O:53][N:54]=4)[N:47]([CH2:48][CH3:49])[C:41]=3[CH:40]=2)[CH:35]=[CH:36][CH:37]=1>CN(C=O)C.O.CCOC(C)=O>[NH2:55][C:51]1[C:50]([C:46]2[N:47]([CH2:48][CH3:49])[C:41]3[CH:40]=[C:39]([O:38][C:34]4[CH:33]=[C:32]([NH:31][C:1]([C:2]5[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=5)=[O:9])[CH:37]=[CH:36][CH:35]=4)[N:44]=[CH:43][C:42]=3[N:45]=2)=[N:54][O:53][N:52]=1

Participants

8

Reactant 4

HCID 938Nicotinic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide2×HCID 757711-HydroxybenzotriazoleHCID 11404963HCID 11404963, compound

Product 1

HCID 11442085HCID 11442085, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a room temperature suspension of 0.036 g of nicotinic acid (0.30 mmols) and 0.061 g of EDCI (0.32 mmols) in dry DMF (2.0 mL) was added 0.043 g of HOBt (0.32 mmols). After stirring for 10 min., 0.10 g of the product of Example 3 (0.3 mmols) was added to the reaction mixture. After stirring for 1 h, the reaction was treated with an additional 0.061 g of EDCI (0.32 mmols). The mixture was allowed to stir for 27 h at rt. The reaction mixture was diluted with 2 mL of water and 10 mL of EtOAc. The layers were separated, and the organic layer was washed with water. The organics were dried over MgSO4, filtered, and concentrated. The yellow residue was washed with methanol to yield an off-white solid (73 mg, 57%). MS (ES+) m/e 444 [M+H]+.

Workup

  1. stirringAfter stirring for 1 h
  2. stirringto stir for 27 h at rt
  3. customThe layers were separated
  4. washthe organic layer was washed with water
  5. dry with materialThe organics were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washThe yellow residue was washed with methanol

Sources & evidence

ORD record
ord-4c9a21a39c0a419797fb2faee67f38ad
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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