Water → (E)-tert-Butyl 4-(8-morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-b]pyridazin-3-yl)benzoate

HRID 718571Notes

Reaction equation

[CH:1]([C:3]1[N:4]=[C:5]2[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:9][CH:8]=[N:7][N:6]2[C:17]=1[C:18]1[CH:30]=[CH:29][C:21]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:20][CH:19]=1)=O.[CH3:31][C:32]1[CH:41]=[CH:40][C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[N:33]=1.Cl[Si](C)(C)C.O>CN(C=O)C>[O:14]1[CH2:15][CH2:16][N:11]([C:10]2[C:5]3[N:6]([C:17]([C:18]4[CH:30]=[CH:29][C:21]([C:22]([O:24][C:25]([CH3:27])([CH3:28])[CH3:26])=[O:23])=[CH:20][CH:19]=4)=[C:3](/[CH:1]=[CH:31]/[C:32]4[CH:41]=[CH:40][C:39]5[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=5)[N:33]=4)[N:4]=3)[N:7]=[CH:8][CH:9]=2)[CH2:12][CH2:13]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of compound 5f (0.68 g, 1.7 mmol) and 2-methylquinoline (0.26 mL, 2.0 mmol) in DMF (5 mL) was added chlorotrimethylsilane (0.64 mL, 5.0 mmol) dropwise. The resulting mixture was stirred at 90° C. for 2 h. The reaction mixture was cooled, and water (20 mL) was added. The precipitated solid was collected by filtration, washed with MeOH (2×5 mL), and dried under high vacuum. Compound 5g was obtained as an orange solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C32H31 N5O3: 534.2 (M+H). found: 534.4.

Workup

temperatureThe reaction mixture was cooled
filtrationThe precipitated solid was collected by filtration
washwashed with MeOH (2×5 mL)
customdried under high vacuum

Sources & evidence

ORD record: ord-44756b00f1f54f2c985b360c3013a4ee
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193736B2

Reaction notes

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