Diisopropylethylamine → HCID 86716517, compound

HRID 1501345Notes

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

Participants

Conditions

Temperature: 120 °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] (391 mg, ˜80% purity, 0.710 mmol, 1.0 eq), 6-methoxy-4,5-dimethylpyridazin-3-amine (that was prepared in a manner analgous to that described for Intermediate Example Int-34, Step 1, 108 mg, 0.710 mmol, 1.0 eq) and N,N-diisopropylethylamine (140 μL, 0.780 mmol, 1.1 eq) in butyronitrile (4.9 mL) was heated for 3 hours at 120° C. On cooling the reaction mixture was concentrated in vacuo. The crude mixture was purified via MPLC (Biotage Isolera; 25 g SNAP cartridge: hexane/EtOAc 9/1→hexane/EtOAc 2/3) to give 105 mg (28% 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 MPLC (Biotage Isolera; 25 g SNAP cartridge: hexane/EtOAc 9/1→hexane/EtOAc 2/3)

Sources & evidence

ORD record: ord-2c65ecae392f44fdb2c37ed73277157d
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206185B2

Reaction notes

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