Potassium Carbonate → HCID 71727039, compound

HRID 870726Notes

Reaction equation

Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][N:14]3[CH2:18][CH2:17][N:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:15]3=[O:23])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.Cl.[NH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=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>[NH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:2]2[N:6]3[N:7]=[C:8]([NH:11][CH2:12][CH2:13][N:14]4[CH2:18][CH2:17][N:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:15]4=[O:23])[CH:9]=[CH:10][C:5]3=[N:4][CH:3]=2)=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 1-[2-(3-bromo-imidazo[1,2-b]pyridazin-6-ylamino)-ethyl]-3-tert-butyl-imidazolidin-2-one (75 mg, 0.2 mmol), (4-aminomethylphenyl)boronic acid hydrochloride (49 mg, 0.26 mmol), K2CO3 (83 mg, 0.6 mmol) and dichlorobis(triphenylphosphine)palladium(II) (7 mg, 0.01 mmol) in MeCN/water (2.8 ml/0.7 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 (64.8 mg). 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.26 (s, 9H) 3.24-3.31 (m, 4H) 3.40 (t, J=5.95 Hz, 2H) 3.52 (t, J=5.95 Hz, 2H) 4.17 (s, 2H) 6.70 (d, J=9.70 Hz, 1H) 7.54-7.63 (m, 3H) 7.77 (s, 1H) 8.19-8.23 (m, 2H) 8.56 (s, 1H). LRMS (ESI) m/z 408.4 [(M+H)]+, calc'd for C22H29N7O: 407.52.

Workup

filtrationfiltered

Sources & evidence

ORD record: ord-4207636c4a644d62b2de654d2ac25ba0
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969565B2

Reaction notes

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