Ethanol → (S)-2-[4-(1-Hydroxymethyl-2-phenyl-ethylamino)-2-oxo-1,2-dihydro-pyridin-3-yl]-7-methyl-3H-benzimidazole-5-carboximidic ethyl ester

HRID 1354643Notes

Reaction equation

[OH:1][CH2:2][C@@H:3]([NH:11][C:12]1[CH:17]=[CH:16][NH:15][C:14](=[O:18])[C:13]=1[C:19]1[NH:20][C:21]2[CH:27]=[C:26]([C:28]#[N:29])[CH:25]=[C:24]([CH3:30])[C:22]=2[N:23]=1)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:31]([OH:33])[CH3:32]>>[CH2:31]([O:33][C:28]([C:26]1[CH:25]=[C:24]([CH3:30])[C:22]2[N:23]=[C:19]([C:13]3[C:14](=[O:18])[NH:15][CH:16]=[CH:17][C:12]=3[NH:11][C@H:3]([CH2:2][OH:1])[CH2:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)[NH:20][C:21]=2[CH:27]=1)=[NH:29])[CH3:32]

Participants

Reactant 2

HCID 702Ethanol

HCID 136380434(S)-2-[4-(1-Hydroxymethyl-2-phenyl-ethylamino)-2-oxo-1,2-dihydro-pyridin-3-yl]-7-methyl-3H-benzimidazole-5-carbonitrile

Product 1

HCID 136007981(S)-2-[4-(1-Hydroxymethyl-2-phenyl-ethylamino)-2-oxo-1,2-dihydro-pyridin-3-yl]-7-methyl-3H-benzimidazole-5-carboximidic ethyl ester

Procedure

To a suspension of (S)-2-[4-(1-hydroxymethyl-2-phenyl-ethylamino)-2-oxo-1,2-dihydro-pyridin-3-yl]-7-methyl-3H-benzimidazole-5-carbonitrile (0.8 g, 2.0 mmol) in ethanol (anhydrous, 80 mL) was bubbled HCl (anhydrous) at 0° C. until saturation. The mixture became a clear solution after a few minutes of bubbling and the solution was stirred at room temperature for 14 h. After concentration in vacuo, the crude product (0.89 g, 100%) was directly used for the next step without purification. LCMS (M+H)+ m/z 446 (t=1.55 min).

Workup

customwas bubbled HCl (anhydrous) at 0° C. until saturation
customafter a few minutes
customof bubbling
concentrationAfter concentration in vacuo
customthe crude product (0.89 g, 100%) was directly used for the next step without purification
customLCMS (M+H)+ m/z 446 (t=1.55 min)

Sources & evidence

ORD record: ord-dc5d05c8189a42598791124c8ea7217f
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07223757B2

Reaction notes

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