Potassium Carbonate → HCID 86696440, compound

HRID 870734Notes

Reaction equation

Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][N:14]3[C@H:18]([CH:19]([CH3:21])[CH3:20])[CH2:17][O:16][C:15]3=[O:22])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.Cl.[NH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C([O-])([O-])=O.[K+].[K+]>CC#N.O.CC#N.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:2]2[N:6]3[N:7]=[C:8]([NH:11][CH2:12][CH2:13][N:14]4[C@H:18]([CH:19]([CH3:21])[CH3:20])[CH2:17][O:16][C:15]4=[O:22])[CH:9]=[CH:10][C:5]3=[N:4][CH:3]=2)=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of (R)-3-[2-(3-bromo-imidazo[1,2-b]pyridazin-6-ylamino)-ethyl]-4-isopropyl-oxazolidin-2-one (95 mg, 0.26 mmol), (4-aminomethylphenyl)boronic acid hydrochloride (63.7 mg, 0.34 mmol), K2CO3 (108 mg, 0.78 mmol) and dichlorobis(triphenylphosphine)palladium(II) (9.1 mg, 0.013 mmol) in MeCN/water (3.2 ml/0.8 ml) was heated in a microwave at 150° C. for 15 min. The reaction mixture was diluted with MeCN and filtered. The filtrate was subjected to preparative HPLC to give the titled compound as HCOOH salt (86.3 mg). 1H NMR (400 MHz, METHANOL-d4) ppm 0.84 (dd, J=6.95, 0.88 Hz, 6H) 2.09 (td, J=6.95, 3.54 Hz, 1H) 3.26-3.31 (m, 1H) 3.59-3.71 (m, 2H) 3.85 (dt, J=13.96, 6.79 Hz, 1H) 3.95 (ddd, J=8.65, 5.24, 3.54 Hz, 1H) 4.11-4.19 (m, 4H) 6.74 (d, J=9.60 Hz, 1H) 7.58 (d, J=8.34 Hz, 2H) 7.68 (d, J=9.85 Hz, 1H) 7.81 (s, 1H) 8.21-8.26 (m, 2H) 8.52 (s, 1H). LRMS (ESI) m/z 395.3 [(M+H)]+, calc'd for C21H26N6O2: 394.48.

Workup

filtrationfiltered

Sources & evidence

ORD record: ord-292f4158ffc74e499cca46a784da0760
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969565B2

Reaction notes

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