Water → HCID 178509707, compound

HRID 931251Notes

Reaction equation

HRID 931251 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:5]=[CH:6][C:7]([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:8][C:9]=1[NH2:10].[CH:24]([C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[C:29]#[N:30])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+].O>C(O)C>[N:19]1([C:17]([C@@H:13]2[CH2:14][CH2:15][CH2:16][N:11]([C:7]3[N:8]=[C:9]4[NH:10][C:24]([C:26]5[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=5)[C:29]#[N:30])=[N:3][C:4]4=[CH:5][CH:6]=3)[CH2:12]2)=[O:18])[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 24489Sodium DithioniteHCID 90670m-FormylbenzonitrileHCID 89854051(R)-(1-(5,6-Diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone dihydrochloride2×

Product 1

HCID 178509707HCID 178509707, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (R)-(1-(6-amino-5-nitropyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone (Intermediate 1, Step 3) (50 mg, 0.15 mmol) and 3-formylbenzonitrile (34 mg, 0.31 mmol) in ethanol (2 mL) were added sodium dithionite (52 mg, 0.4 mmol), and water (0.5 mL). After 20 h at 80° C., the mixture was concentrated. The residue was partitioned between water and ethyl acetate. The organic layer was concentrated under reduced pressure and the resulting residue was purified by preparative TLC to afford (R)-3-(5-(3-(pyrrolidine-1-carbonyl)piperidin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)benzonitrile as a yellow solid (40 mg, 81%). MS (ES+APCI) (M+H) 401.0; HPLC retention time 4.016 min (Method I).

Workup

  1. concentrationthe mixture was concentrated
  2. customThe residue was partitioned between water and ethyl acetate
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customthe resulting residue was purified by preparative TLC

Sources & evidence

ORD record
ord-a3b43cb9ce3e4322a8c507c04c19d3c3
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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