Ethyl Acetate → HCID 50913155, compound

HRID 1942094Notes

Reaction equation

Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C@H:11]([C:13]3[C:14]([F:24])=[C:15]4[C:19](=[CH:20][C:21]=3[F:22])[N:18]([CH3:23])[N:17]=[CH:16]4)[CH3:12])=[CH:9][N:10]=2)[N:7]=1.[F-].[K+].CCO[C:30]([CH3:32])=[O:31]>CN1C(=O)CCC1>[F:24][C:14]1[C:13]([C@@H:11]([C:8]2[N:6]3[N:7]=[C:2]([N:10]4[CH2:9][CH2:8][N:6]([CH3:5])[C:30](=[O:31])[CH2:32]4)[CH:3]=[CH:4][C:5]3=[N:10][CH:9]=2)[CH3:12])=[C:21]([F:22])[CH:20]=[C:19]2[C:15]=1[CH:16]=[N:17][N:18]2[CH3:23]

Participants

Conditions

Temperature: 180 °C

Procedure

6-Chloro-3-[(S)-1-(4,6-difluoro-1-methyl-1H-indazol-5-yl)-ethyl]-imidazo[1,2-b]pyridazine (Intermediate Q, 50.0 mg, 0.144 mmol), KF (42.6 mg, 0.719 mmol) and 1-methylperazine-2-one hydrochloride (67.0 mg, 0.431 mmol) were suspended in NMP (0.4 mL). The RM was stirred at 180° C. for 4 h. The mixture was diluted with EtOAc and washed with NaHCO3 10% (2×) and water (4×). The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography and afforded the title compound as a light brown foam (tR 3.75 min (conditions 5), (tR 11.35 min (conditions 2), MH+=425.9, 1H-NMR in DMSO-d6: 8.07 (s, 1H); 7.80 (d, 1H); 7.52 (s, 1H); 7.36 (d, 1H); 7.05 (d, 1H); 4.85 (m, 1H); 4.01 (d, 1H); 3.95 (s, 3H); 3.78 (d, 1H); 3.62 (m, 2H); 3.27 (m, 2H); 2.81 (s, 3H); 1.79 (d, 3H)).

Workup

washwashed with NaHCO3 10% (2×) and water (4×)
dry with materialThe combined organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-5964a6c5196a4577a394b9f0580c9d33
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389526B2

Reaction notes

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