Potassium Carbonate → HCID 54591079, compound

HRID 2401135Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:25][CH2:24][C:11]2([C:15](=[O:16])[N:14]([C:17]3[CH:18]=[N:19][C:20](Cl)=[N:21][CH:22]=3)[CH2:13][CH2:12]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:27][C@H:28]1[CH2:32][CH2:31][CH2:30][N:29]1[C@H:33]1[CH2:37][CH2:36][NH:35][CH2:34]1.C([O-])([O-])=O.[K+].[K+].C([O-])(O)=O.[Na+]>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:25][CH2:24][C:11]2([C:15](=[O:16])[N:14]([C:17]3[CH:18]=[N:19][C:20]([N:35]4[CH2:36][CH2:37][C@H:33]([N:29]5[CH2:30][CH2:31][CH2:32][C@@H:28]5[CH3:27])[CH2:34]4)=[N:21][CH:22]=3)[CH2:13][CH2:12]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 2-(2-chloro-pyrimidin-5-yl)-1-oxo-2,8-diaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester (102 mg, 0.28 mmol) in DMSO (2 mL) was added (2S,3′S)-2-methyl-[1,3′]bipyrrolidinyl hydrochloride (350 mg, 1.23 mmol), and K2CO3 (920 mg, 6.65 mmol). The reaction mixture was heated to 90° C. with stirring for 18 hours. The reaction was cooled to rt and was added NaHCO3 (aq) (10 mL), extracted with EtOAc (2×10 mL), washed organics with brine (5 mL), concentrated and purified by flash column chromatography (5% 7N NH3 in MeOH/CH2Cl2) to obtain 18.9 mg (15% yield) of the title compound.

Workup

temperatureThe reaction was cooled to rt
extractionextracted with EtOAc (2×10 mL)
washwashed organics with brine (5 mL)
concentrationconcentrated
custompurified by flash column chromatography (5% 7N NH3 in MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-bc3fdf7f2cd6428db5b78bf9ba612ecb
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796278B2

Reaction notes

Loading…