Acetic Acid → HCID 178472505, compound

HRID 931245Notes

Reaction equation

HRID 931245 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH2:14][CH2:13][CH2:12][C@@H:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10]2)=[N:6][C:7]=1[NH2:8].[CH:20]1([C:23]2[N:28]=[C:27]([CH:29]=O)[CH:26]=[CH:25][CH:24]=2)[CH2:22][CH2:21]1.[S].C(O)(=O)C>C(O)C>[CH:20]1([C:23]2[N:28]=[C:27]([C:29]3[NH:8][C:7]4=[N:6][C:5]([N:9]5[CH2:14][CH2:13][CH2:12][C@@H:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10]5)=[CH:4][CH:3]=[C:2]4[N:1]=3)[CH:26]=[CH:25][CH:24]=2)[CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5362487SulfurHCID 193617216-CyclopropylpicolinaldehydeHCID 131735159(R)-ethyl 1-(5,6-diaminopyridin-2-yl)piperidine-3-carboxylate

Product 1

HCID 178472505HCID 178472505, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (R)-ethyl 1-(5,6-diaminopyridin-2-yl)piperidine-3-carboxylate (250 mg, 0.686 mmol) in ethanol (15 mL) was added 6-cyclopropylpicolinaldehyde (55 mg, 0.823 mmol), sulfur (43 mg, 1.372 mmol) and acetic acid (1.5 mL) at room temperature. The reaction mixture was stirred at 80° C. for 18 h. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organics were concentrated under reduced pressure and the crude material was purified via preparative TLC (80% ethyl acetate in petroleum ether) to afford (R)-ethyl 1-(2-(6-cyclopropylpyridin-2-yl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidine-3-carboxylate (180 mg). MS (ES+APCI) (M+H) 392.2; LCMS retention time 3.757 min (Method J).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organics were concentrated under reduced pressure
  3. customthe crude material was purified via preparative TLC (80% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-f4f0b2bb5dff4230a1bfd575a7214a30
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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