Acetic Acid → N-[3-Benzyl-2-(1,5-dimethyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3H-benzoimidazol-5-yl]-acetamide

HRID 930521Notes

Reaction equation

C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([C:17]2[CH:22]=[C:21]([CH3:23])[C:20](=[O:24])[N:19]([CH3:25])[CH:18]=2)=O)=[C:10]([NH:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:9]=1)(C)(C)C.[C:35](O)(=[O:37])[CH3:36]>>[CH2:27]([N:26]1[C:10]2[CH:9]=[C:8]([NH:7][C:35](=[O:37])[CH3:36])[CH:13]=[CH:12][C:11]=2[N:14]=[C:15]1[C:17]1[CH:22]=[C:21]([CH3:23])[C:20](=[O:24])[N:19]([CH3:25])[CH:18]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

Reactant 2

HCID 176Acetic Acid

HCID 117894045{3-Benzylamino-4-[(1,5-dimethyl-6-oxo-1,6-dihydro-pyridine-3-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester

Product 1

HCID 117891922N-[3-Benzyl-2-(1,5-dimethyl-6-oxo-1,6-dihydro-pyridin-3-yl)-3H-benzoimidazol-5-yl]-acetamideYield 90%

Conditions

Temperature: 150 °C

Procedure

{3-Benzylamino-4-[(1,5-dimethyl-6-oxo-1,6-dihydro-pyridine-3-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester I-9″ (4.000 g; 8.648 mmol) is suspended in acetic acid (5.190 g; 86 mmol) in a microwave vial and heated in the microwave at 150° C. for 1 h. The reaction mixture is then concentrated under reduced pressure. The residue is added to ice water, precipitation occurs. The precipitate is filtered off and dried under vacuum. The residue is used in the next step without further purification. (Yield: 90%, 3.000 g; 7.763 mmol)

Workup

concentrationThe reaction mixture is then concentrated under reduced pressure
additionThe residue is added to ice water, precipitation
filtrationThe precipitate is filtered off
customdried under vacuum
customThe residue is used in the next step without further purification

Sources & evidence

ORD record: ord-e5f70b99f6234ae8ba718157990fd682
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296748B2

Reaction notes

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