HCID 54262809, compound → 4-[3-(5-chloro-2-oxo-2H-[1,2']bipyridinyl-5'-ylmethyl)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridin-4-yl]-benzonitrile

HRID 1421719Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][C:11]2[N:14]=[CH:15][N:16]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([N:24]4[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]4=[O:31])=[N:22][CH:23]=3)[C:10]=2[CH:9]1[C:32]1[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[CH:34][CH:33]=1)=O)(C)(C)C>CCOC(C)=O>[Cl:30][C:28]1[CH:27]=[CH:26][C:25](=[O:31])[N:24]([C:21]2[CH:20]=[CH:19][C:18]([CH2:17][N:16]3[C:10]4[CH:9]([C:32]5[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[CH:34][CH:33]=5)[NH:8][CH2:13][CH2:12][C:11]=4[N:14]=[CH:15]3)=[CH:23][N:22]=2)[CH:29]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3-(5-Chloro-2-oxo-2H-[1,2']bipyridinyl-5'-ylmethyl)-4-(4-cyano-phenyl)-3,4,6,7-tetrahydro-imidazo[4,5-c]pyridine-5-carboxylic acid tert-butyl ester (0.27 g, 0.50 mmol) was dissolved in EtOAc, cooled to 0° C., degassed with Ar, and saturated with anh. HCl gas. The solution was concentated in vacuo and the diastereomers separated using a Chiralcel OD column (25 cm×2 cm, 10/90-0/100 Hexane/EtOH with 0.1% DEA, flow 5.0 mL/min) followed by enantiomer seperation using a Delta Pak C18 column (0-100% H2O (0.1% NH4HCO3)/CH3CN) to give the title compound. 1H NMR (CDCl3); δ 8.01-7.96 (m, 3H), 7.60 (d, 2H, J=8 Hz), 7.54 (s, 1H), 7.37-7.30 (m, 2H), 7.27-7.21 (m, 3H), 6.61 (d, 1H, J=10 Hz), 4.85 (d, 1H, J=16 Hz), 4.79 (s, 1H), 4.45 (s, 1H, J=16 Hz), 3.05-3.01 (m, 2H), 2.80-2.77 (m, 2H).

Workup

customdegassed with Ar
customthe diastereomers separated
customfollowed by enantiomer seperation

Sources & evidence

ORD record: ord-ce01431f9aaa47d38019493999886dd1
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06077853

Reaction notes

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