Diisopropylethylamine → HCID 70856623, compound

HRID 1501347Notes

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][C:30]1[C:35]([CH3:36])=[C:34]([S:37][CH3:38])[N:33]=[N:32][C:31]=1[NH2:39].C(N(CC)C(C)C)(C)C>C(#N)CCC>[CH3:36][C:35]1[C:34]([S:37][CH3:38])=[N:33][N:32]2[C:2]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=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]([CH3:21])([CH3:20])[CH3:19])[CH2:14][CH2:13][CH2:12]4)=[CH:7][CH:6]=3)[N:39]=[C:31]2[C:30]=1[CH3:29]

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] (540 mg, ˜80% purity, 0.970 mmol, 1.0 eq), 4,5-dimethyl-6-(methylsulfanyl)-pyridazin-3-amine (that was prepared in a manner analgous to that described for Intermediate Example Int-35, Step 1, 181 mg, ˜50% purity, 1.07 mmol, 1.1 eq) and N,N-diisopropylethylamine (170 μL, 0.970 mmol, 1.1 eq) in butyronitrile (4.7 mL) was heated for 4 hours at 125° C. On cooling the reaction mixture was concentrated in vacuo. The crude mixture was purified via reversed phase preparative HPLC to give 105 mg (19% 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 reversed phase preparative HPLC

Sources & evidence

ORD record: ord-30b75765495b4e5db48e5a1ddc7ac418
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206185B2

Reaction notes

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