Water → HCID 86721468, compound

HRID 869609Notes

Reaction equation

Cl[C:2]1[C:3]2[N:4]([C:8]([CH2:14][C:15]3[CH:34]=[CH:33][C:18]4/[C:19](=[C:29](/[CH3:32])\[C:30]#[N:31])/[C:20]5[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:21]=5[O:22][CH2:23][C:17]=4[CH:16]=3)=[C:9]([CH:11]3[CH2:13][CH2:12]3)[N:10]=2)[CH:5]=[CH:6][N:7]=1.[CH3:35][NH:36][CH3:37].C1COCC1.O>C1COCC1>[CH:11]1([C:9]2[N:10]=[C:3]3[C:2]([N:36]([CH3:37])[CH3:35])=[N:7][CH:6]=[CH:5][N:4]3[C:8]=2[CH2:14][C:15]2[CH:34]=[CH:33][C:18]3/[C:19](=[C:29](/[CH3:32])\[C:30]#[N:31])/[C:20]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:21]=4[O:22][CH2:23][C:17]=3[CH:16]=2)[CH2:12][CH2:13]1

Participants

Conditions

Temperature: 100 °C

Procedure

[step 6] (E)-2-{8-[(8-chloro-2-cyclopropylimidazo[1,2-a]pyrazin-3-yl)methyl]-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrile (0.2 g, 0.43 mmol) obtained in step 5 was dissolved in THF (1.4 mL), and 2 mol/L dimethylamine THF solution (1.7 mL, 3.4 mmol) was added. The mixture was stirred with heating at 100° C. for 1.5 hr in an Emrys Optimizer microwave synthesizer. Water was added to the mixture, and the mixture was extracted 3 times with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane/ethyl acetate=100/0 v/v-50/50 v/v) to give the title compound (0.18 g, 87%).

Workup

extractionthe mixture was extracted 3 times with ethyl acetate
dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (heptane/ethyl acetate=100/0 v/v-50/50 v/v)

Sources & evidence

ORD record: ord-51c6d43f9845496abcaf272d1c216879
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969345B2

Reaction notes

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