Propionic Acid → HCID 86694207, compound

HRID 707349Notes

Reaction equation

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

Participants

Reactant 3

HCID 1032Propionic Acid

HCID 74613Tetramethyl orthocarbonate

HCID 86694206HCID 86694206, compound

Product 1

HCID 86694207HCID 86694207, compoundYield 14.4%

Conditions

Temperature: 90 °C

Procedure

N2-[4-((1H-Benzo[d]imidazol-2-yl)amino)cyclohexyl)pyridine-2,3-diamine (320 mg, 0.99 mmol) was combined with tetramethylorthocarbonate (2 mL) and propionic acid (8 mg), the mixture was 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 N-(4-(2-methoxy-3H-imidazo[4,5-b]pyridin-3-yl)cyclohexyl)-1H-benzo[d]imidazol-2-amine (50 mg, 0.14 mmol, 14.4% yield). M+1: 380.

Workup

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

Sources & evidence

ORD record: ord-9a179958798c488aa5cfe5d4fc09f815
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174992B2

Reaction notes

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