Propionic Acid → HCID 86694196, compound

HRID 707337Notes

Reaction equation

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

Participants

Reactant 3

HCID 1032Propionic Acid

HCID 74613Tetramethyl orthocarbonate

HCID 86694197HCID 86694197, compound

Product 1

HCID 86694196HCID 86694196, compoundYield 9.8%

Conditions

Temperature: 90 °C

Procedure

(4-((3-Amino-pyridin-2-yl)amino)piperidin-1-yl)(1H-benzo[d]imidazol-2-yl)methanone (520 mg, 1.55 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 (1H-benzo[d]imidazol-2-yl)(4-(2-methoxy-3H-imidazo[4,5-b]pyridin-3-yl)piperidin-1-yl)methanone (57 mg, 0.15 mmol, 9.8% yield). M+1: 377.

Workup

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

Sources & evidence

ORD record: ord-674f43c791214815828db5ae3067e347
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174992B2

Reaction notes

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