Diisopropylethylamine → HCID 89701563, compound

HRID 1774942Notes

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]([C:31]1[N:32]=[C:33]([O:38][CH3:39])[C:34]([NH2:37])=[N:35][CH:36]=1)[CH3:30].C(N(C(C)C)CC)(C)C>C(#N)CCC>[CH2:29]([C:31]1[N:32]=[C:33]([O:38][CH3:39])[C:34]2[N:35]([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:37]=2)[CH:36]=1)[CH3:30]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of crude tert-butyl (1-{4-[bromo(phenyl)acetyl]phenyl}cyclobutyl)carbamate [Int-1-A] (288 mg, 0.55 mmol, 1.0 eq), 5-ethyl-3-methoxypyrazin-2-amine (84.4 mg, 0.55 mmol, 1 eq.; see step 2) and diisopropylethylamine (0.110 mL, 0.61 mmol, 1.1 eq) in 3.9 mL butyronitrile was heated at 120° C. for 20 hours. The reaction mixture was concentrated in vacuo. The crude mixture was purified via MPLC (Isolera, 50 g Snap-cartridge, eluent:hexane→hexane/ethyl acetate 1/1) to deliver 128 mg (25%) of the title compound in approximately 50-60 purity (UPLC). The title compound observed this way was forwarded to the next step without further purification.

Workup

concentrationThe reaction mixture was concentrated in vacuo
customThe crude mixture was purified via MPLC (Isolera, 50 g Snap-cartridge, eluent:hexane→hexane/ethyl acetate 1/1)
customwas forwarded to the next step without further purification

Sources & evidence

ORD record: ord-ecaf5e863c3040e8a92d571a6e8f2f2f
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260435B2

Reaction notes

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