Hydrochloric Acid → HCID 46853632, compound

HRID 1628274Notes

Reaction equation

C[O:2][C:3]1[C:8]([NH:9][C:10](=[O:29])[C@@H:11]([NH:19][C:20]2([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[CH2:22][CH2:21]2)[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][C:6]([C:30]2[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=2)=[CH:5][N:4]=1.Cl>O1CCOCC1>[O:2]=[C:3]1[C:8]([NH:9][C:10](=[O:29])[C@@H:11]([NH:19][C:20]2([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[CH2:22][CH2:21]2)[CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:7][C:6]([C:30]2[CH:31]=[CH:32][N:33]=[CH:34][CH:35]=2)=[CH:5][NH:4]1

Participants

Conditions

Temperature: 50 °C

Procedure

(S)—N-(2-methoxy-5-(pyridin-4-yl)pyridin-3-yl)-3-phenyl-2-(1-(pyridin-2-yl)cyclopropylamino)propanamide 11.1 (38.5 mg, 83 μmol) was dissolved in 4.5 mL dioxane. Concentrated HCl (0.5 ml, 16456 μmol) was added. The reaction was heated to 50° C. for 2.5 h. LC/MS showed the completion of the reaction. The reaction was concentrated, neutralized with saturated NaHCO3, then extracted with 30% IPA/CHCl3 once. The organic layer was concentrated and purified by silica gel chromatography to afford 33 mg (89%) of (S)—N-(2-oxo-5-(pyridin-4-yl)-1,2-dihydropyridin-3-yl)-3-phenyl-2-(1-(pyridin-2-yl)cyclopropylamino)propanamide (35.1). 1H NMR (400 MHz, MeOH) δ ppm 8.82 (d, J=2.74 Hz, 1H) 8.48-8.63 (m, 2H) 8.19-8.36 (m, 1H) 7.68 (d, J=2.74 Hz, 1H) 7.61-7.65 (m, 2H) 7.52-7.59 (m, 1H) 7.20-7.26 (m, 3H) 7.08-7.16 (m, 4H) 3.58 (dd, J=8.61, 4.70 Hz, 1H) 3.04 (dd, J=13.69, 4.69 Hz, 1H) 2.83 (dd, J=13.69, 9.00 Hz, 1H) 1.06-1.21 (m, 3H) 0.82-0.91 (m, 1H).

Workup

customthe completion of the reaction
concentrationThe reaction was concentrated
extractionextracted with 30% IPA/CHCl3 once
concentrationThe organic layer was concentrated
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-d0f3ae08aeaa4718a638895d61a24993
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785468B2

Reaction notes

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