Propionic Acid → HCID 86694200, compound

HRID 707340Notes

Reaction equation

HRID 707340 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:15][CH2:14][CH:13]([N:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]2[NH2:23])[CH2:12][CH2:11]1.[CH3:24][O:25][C:26](OC)(OC)OC.C(O)(=O)CC>>[CH3:24][O:25][C:26]1[N:16]([CH:13]2[CH2:12][CH2:11][N:10]([C:2]3[S:1][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=3)[CH2:15][CH2:14]2)[C:17]2=[N:23][CH:21]=[CH:20][CH:19]=[C:18]2[N:22]=1

Participants

4

Reactant 3

HCID 1032Propionic AcidHCID 74613Tetramethyl orthocarbonateHCID 86694201HCID 86694201, compound

Product 1

HCID 86694200HCID 86694200, compoundYield 13.4%

Conditions

Temperature
90 °C

Procedure

N1-(1-(Benzo[d]thiazol-2-yl)piperidin-4-yl)pyridine-2,3-diamine (200 mg, 0.61 mmol) was combined with tetramethylorthocarbonate (2 mL) and propionic acid (8 mg) and heated at 90° C. for 2 hours. After that, the reaction solution was concentrated under reduced pressure and the residue was purified by silica chromatography to give 2-(4-(2-methoxy-3H-imidazo[4,5-b]pyridine-3-yl)piperidin-1-yl)benzo[d]thiazole (30 mg, 0.082 mmol, 13.4% yield). M+1: 366.

Workup

  1. concentrationAfter that, the reaction solution was concentrated under reduced pressure
  2. customthe residue was purified by silica chromatography

Sources & evidence

ORD record
ord-ebd381c43e7c4b32829f808969b14e57
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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