Ethyl Acetate → HCID 50913305, compound

HRID 1942099Notes

Reaction equation

Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([C:13]3[C:14]([F:26])=[C:15]4[C:19](=[CH:20][C:21]=3[F:22])[N:18]([CH:23]([CH3:25])[CH3:24])[N:17]=[CH:16]4)[CH3:12])=[CH:9][N:10]=2)[N:7]=1.[F-].[K+].CCO[C:32]([CH3:34])=[O:33]>CN1C(=O)CCC1>[F:26][C:14]1[C:13]([CH:11]([C:8]2[N:6]3[N:7]=[C:2]([N:10]4[CH2:9][CH2:8][N:6]([CH3:5])[C:32](=[O:33])[CH2:34]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[CH:23]([CH3:25])[CH3:24]

Participants

Conditions

Temperature: 180 °C

Procedure

(rac)-6-chloro-3-(1-(4,6-difluoro-1-isopropyl-1H-indazol-5-yl)ethyl)imidazo[1,2-b]pyridazine (Intermediate U, 56.4 mg, 0.15 mmol), KF (43.6 mg, 0.75 mmol) and 1-methylperazine-2-one hydrochloride (51.4 mg, 0.45 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 4.06 min (conditions 5), MH+=454.3, 1H-NMR in DMSO-d6: 8.09 (s, 1H); 7.81 (d, 1H); 7.53 (s, 1H); 7.43 (d, 1H); 7.05 (d, 1H), 4.86 (m, 2H); 4.03 (d, 1H); 3.81 (d, 1H); 3.64 (m, 2H); 3.24 (m, 2H); 2.80 (s, 3H); 1.79 (d, 3H), 1.41 (m, 6H)).

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-1fcd4c2d16554707be8a91fca52d6551
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389526B2

Reaction notes

Loading…