Water → (E)-4-(8-Morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-b]pyridazin-3-yl)aniline

HRID 718576Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]3[N:15]=[CH:16][CH:17]=[C:18]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[C:13]3=[N:12][C:11]=2/[CH:25]=[CH:26]/[C:27]2[CH:36]=[CH:35][C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:28]=2)=[CH:6][CH:5]=1)([O-])=O.O.[OH-].[Na+]>C(O)(=O)C.[Fe]>[O:22]1[CH2:21][CH2:20][N:19]([C:18]2[C:13]3[N:14]([C:10]([C:7]4[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=4)=[C:11](/[CH:25]=[CH:26]/[C:27]4[CH:36]=[CH:35][C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[N:28]=4)[N:12]=3)[N:15]=[CH:16][CH:17]=2)[CH2:24][CH2:23]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of compound 10a (0.85 g, 1.8 mmol) in acetic acid (20 mL) was added iron powder (0.50 g, 8.9 mmol). The reaction mixture was stirred at 80° C. for 2 h, and allowed to cool to rt. The reaction mixture was treated with water, and the pH of the solution was adjusted to ca. pH 7 using 3 N NaOH solution. The mixture was extracted with DCM (3×100 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated to obtain compound 10b as a dark red solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C27H24N6O: 449.2 (M+H). found: 449.1.

Workup

temperatureto cool to rt
extractionThe mixture was extracted with DCM (3×100 mL)
dry with materialThe combined organic layers were dried over MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-8038bc41af7844fabf04241f4147e769
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193736B2

Reaction notes

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