Triethylamine → Tert-butyl 4-(6-bromopyrazin-2-yl)-1,4-diazepane-1-carboxylate

HRID 57869Notes

Reaction equation

Br[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Br:8])[N:3]=1.[N:9]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C(N(CC)CC)C>CC(O)C>[Br:8][C:4]1[N:3]=[C:2]([N:12]2[CH2:13][CH2:14][CH2:15][N:9]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:10][CH2:11]2)[CH:7]=[N:6][CH:5]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 2,6-dibromopyrazine (5.0198 mmol; 1194.1 mg), tert-butyl 1,4-diazepane-1-carboxylate (5.271 mmol; 1055.6 mg), and triethylamine (15.06 mmol; 1539 mg; 2.12 mL) in IPA (10 mL) in a sealed pressure vial was heated at 120° C. overnight. The mixture was cooled to room temperature, and then concentrated. The residue was purified on silica elute with 0 to 100% EtOAc in Heptane to afford tert-butyl 4-(6-bromopyrazin-2-yl)-1,4-diazepane-1-carboxylate (1.6965 g, 95%). MS (ESI) m/z: 357 [M+H]+

Workup

temperatureThe mixture was cooled to room temperature
concentrationconcentrated
customThe residue was purified on silica
washelute with 0 to 100% EtOAc in Heptane

Sources & evidence

ORD record: ord-ac492c5ac66b4286b63aa69dc74586dc
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434725B2

Reaction notes

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