Pyrrolidine → HCID 86691830, compound

HRID 1616220Notes

Reaction equation

CS(O[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[C:9]([C:15]2[N:20]=[C:19]3[N:21]([CH3:30])[C:22](=[O:29])[N:23]([CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:18]3=[CH:17][CH:16]=2)[CH:8]=1)(=O)=O.[NH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1.C(N(C(C)C)CC)(C)C>CN1C(=O)CCC1.CO>[CH3:26][C:25]([CH3:27])([CH3:28])[CH2:24][N:23]1[C:18]2[C:19](=[N:20][C:15]([C:9]3[CH:8]=[C:7]([CH2:6][N:31]4[CH2:35][CH2:34][CH2:33][CH2:32]4)[CH:12]=[CH:11][C:10]=3[C:13]#[N:14])=[CH:16][CH:17]=2)[N:21]([CH3:30])[C:22]1=[O:29]

Participants

Conditions

Temperature: 65 °C

Procedure

To a microwave vial, 4-cyano-3-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]benzyl methanesulfonate (21-1) (20 mg, 0.05 mmol) and pyrrolidine (5 mg, 0.07 mmol) were added and dissolved in NMP (0.25 ml). Diisopropyl ethyl amine (18 mg, 0.14 mmol) was then added and the reaction was heated at 65° C. allowed to stir for 4 hours. The mixture was diluted with methanol and purified using reverse phase chromatography (10-100%, 0.1% TFA in H2O/Acetonitrile); the desired fractions were collected and concentrated to produce 2-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]-4-(pyrrolidin-1-ylmethyl)benzonitrile (13-2). HRMS (M+H)+: observed=404.2456, calculated=404.2445. 1H NMR (400 MHz, CD3 OD): δ 7.91 (s, 1H); 7.83 (d, J=7.9 Hz, 1H); 7.60 (q, J=8.3 Hz, 2H); 7.54 (d, J=8.0 Hz, 1H); 3.82 (s, 2H); 3.77 (s, 2H); 3.55 (s, 3H); 2.64 (m, 4H); 1.85 (m, 4H); 1.06 (s, 9H).

Workup

custompurified
customthe desired fractions were collected
concentrationconcentrated

Sources & evidence

ORD record: ord-70c042b4a99a4a43bde855a62f94ce52
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765784B2

Reaction notes

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