Diisopropylethylamine → HCID 89701581, compound

HRID 1774939Notes

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.[Br:29][C:30]1[N:31]=[C:32]([O:37][CH3:38])[C:33]([NH2:36])=[N:34][CH:35]=1.C(N(C(C)C)CC)(C)C>C(#N)CCC>[Br:29][C:30]1[N:31]=[C:32]([O:37][CH3:38])[C:33]2[N:34]([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])[CH2:14][CH2:13][CH2:12]4)=[CH:7][CH:6]=3)[N:36]=2)[CH:35]=1

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of crude tert-butyl (1-{4-[bromo(phenyl)acetyl]phenyl}cyclobutyl)carbamate [Int-1-A] (203 mg, 0.38 mmol, 1.0 eq), 5-bromo-3-methoxypyrazin-2-amine (74.6 mg, 0.38 mmol, 1 eq.; Jiang, B. et al. Bioorg. Med. Chem. (2001), 9, 1149-1154.) and diisopropylethylamine (0.064 mL, 0.38 mmol, 1.0 eq) in 2.3 mL butyronitril was heated to 120° C. for 17 hours and to 125° C. for 6 h. The reaction mixture was concentrated in vacuo. The crude mixture was purified via preparative HPLC under basic conditions (column: Waters X-Bridge, eluent: ACN/water (15/85)→ACN/water 55/45) to deliver 9 mg (4%) of the title compound.

Workup

concentrationThe reaction mixture was concentrated in vacuo
customThe crude mixture was purified via preparative HPLC under basic conditions (column: Waters X-Bridge, eluent: ACN/water (15/85)→ACN/water 55/45)

Sources & evidence

ORD record: ord-7f2ab62a2d7e4122acd02d10b71a80d6
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260435B2

Reaction notes

Loading…