Ethanol → HCID 178521014, compound

HRID 931271Notes

Reaction equation

HRID 931271 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6]N=[C:4]([N:11]2[CH2:16][CH2:15][CH2:14][C@@H:13]([C:17]([N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[O:18])[CH2:12]2)[N:3]=1.[Br:24][C:25]1[CH:26]=[N:27][CH:28]=[C:29]([CH:32]=1)[CH:30]=O.S(S([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].[CH2:43](O)C>O>[Br:24][C:25]1[CH:32]=[C:29]([C:30]2[NH:1][C:2]3=[N:3][C:4]([N:11]4[CH2:16][CH2:15][CH2:14][C@@H:13]([C:17]([N:19]5[CH2:20][CH2:21][CH2:22][CH2:23]5)=[O:18])[CH2:12]4)=[CH:43][CH:6]=[C:7]3[N:8]=2)[CH:28]=[N:27][CH:26]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 146045Sodium dithionateHCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 89854015Methanone, [(3R)-1-(4-amino-5-nitro-2-pyrimidinyl)-3-piperidinyl]-1-pyrrolidinyl-

Product 1

HCID 178521014HCID 178521014, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of (R)-(1-(4-amino-5-nitropyrimidin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone (0.5 g, 1.5 mmol) in a mixture of ethanol and water were added 5-bromonicotinaldehyde (0.35 g, 1.6 mmol) and sodium dithionate (1.1 g, 5.9 mmol). The reaction mixture was heated to 120° C. for 16 h. The reaction mixture was concentrated and partitioned between water and ethyl acetate. The organics were concentrated under reduced pressure and the resulting crude was purified via preparative TLC to afford (R)-(1-(2-(5-bromopyridin-3-yl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone (400 mg, 60%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between water and ethyl acetate
  3. concentrationThe organics were concentrated under reduced pressure
  4. customthe resulting crude was purified via preparative TLC

Sources & evidence

ORD record
ord-e8fd26ce69f34352b461988a968b53c9
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

Loading…