Diisopropylethylamine → HCID 70856688, compound

HRID 1501349Notes

Reaction equation

Br[CH:2]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1)=O.[CH2:29]([O:31][C:32]1[N:37]=[N:36][C:35]([NH2:38])=[C:34]([CH3:39])[C:33]=1[CH3:40])[CH3:30].C(N(CC)C(C)C)(C)C>C(#N)CCC>[CH2:29]([O:31][C:32]1[C:33]([CH3:40])=[C:34]([CH3:39])[C:35]2[N:36]([C:2]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[C:3]([C:5]3[CH:10]=[CH:9][C:8]([C:11]4([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21])[CH2:12][CH2:13][CH2:14]4)=[CH:7][CH:6]=3)[N:38]=2)[N:37]=1)[CH3:30]

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of crude tert-butyl (1-{4-[bromo(phenyl)acetyl]phenyl}cyclobutyl)carbamate [that was prepared in a manner analgous to that described for Intermediate Example Int-1-A] (300 mg, ˜80% purity, 0.540 mmol, 1.0 eq), 6-ethoxy-4,5-dimethylpyridazin-3-amine (that was prepared in a manner analgous to that described for Intermediate Example Int-36, Step 1, 124 mg, ˜80% purity, 0.590 mmol, 1.1 eq) and N,N-diisopropylethylamine (100 μL, 0.590 mmol, 1.1 eq) in butyronitrile (3.3 mL) was heated for 3.5 hours at 125° C. On cooling the reaction mixture was concentrated in vacuo. The crude mixture was purified via preparative MPLC (Biotage Isolera; 50 g SNAP-cartridge: hexane/EtOAc 9/1→hexane/EtOAc 1/1) to give 220 mg (70% yield) of the title compound.

Workup

customthat was prepared in a manner analgous to
customwas prepared in a manner analgous to
temperatureOn cooling the reaction mixture
concentrationwas concentrated in vacuo
customThe crude mixture was purified via preparative MPLC (Biotage Isolera; 50 g SNAP-cartridge: hexane/EtOAc 9/1→hexane/EtOAc 1/1)

Sources & evidence

ORD record: ord-27e3408ce6f4476db8da9dbec11e0df6
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206185B2

Reaction notes

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