Hydrochloric Acid → HCID 58870822, compound

HRID 1927631Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:27])[CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:16][C:15]=2[F:28])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.Cl[CH:31]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:32]([N:34]([CH2:37][CH3:38])[CH2:35][CH3:36])=[O:33].C([O-])([O-])=O.[K+].[K+]>CO>[CH2:35]([N:34]([CH2:37][CH3:38])[C:32]([CH:31]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[N:8]1[CH2:9][CH:10]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:27])[CH:22]([CH2:23][CH3:24])[CH2:25][CH3:26])=[CH:16][C:15]=2[F:28])[CH2:12][CH2:13]1)=[O:33])[CH3:36]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 4-[4-(2-ethyl-butyrylamino)-2-fluoro-phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (96 mg, 0.25 mmol) in MeOH (5 mL) was added HCl (2 mL, 1 M in Et2O). After 16 h at 25° C., the mixture was concentrated and the residue re-dissolved in DMF (2 mL). The solution was treated with 2-chloro-N,N-diethyl-2-phenyl-acetamide (225 mg, 0.32 mmol) and K2CO3 (138 mg, 1.0 mmol), and was stirred at 25° C. for 16 h. The resulting mixture was purified by PTLC to provide the title compound (25 mg, 21%). MS: 480.4. 1H NMR (CDCl3): 7.57-7.45 (m, 3H), 7.40-7.27 (m, 4H), 7.20-7.06 (m, 2H), 5.90 (s, 1H), 4.43 (s, 1H), 3.55-3.15 (m, 6H), 2.92-2.83 (m, 1H), 2.74-2.64 (m, 1H), 2.53-2.44 (m, 2H), 2.07-1.98 (m, 1H), 1.76-1.47 (m, 4H), 1.17-0.90 (m, 12H).

Workup

concentrationthe mixture was concentrated
dissolutionthe residue re-dissolved in DMF (2 mL)
customThe resulting mixture was purified by PTLC

Sources & evidence

ORD record: ord-40231f8c57d94cc5a3925e3d5813df50
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183239B2

Reaction notes

Loading…