Triethylamine → HCID 66691541, compound

HRID 1808883Notes

Reaction equation

[NH2:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:5]([C:6]#[N:7])=[C:4](F)[CH:3]=1.[N:14]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(N(CC)CC)C>CN(C=O)C>[NH2:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N:17]2[CH2:16][CH2:15][N:14]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18]2)[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-amino-2-fluoro-5-nitrobenzonitrile (132 mg, 0.730 mmol) and tert-butyl piperazine-1-carboxylate (136 mg, 0.730 mmol) in DMF (3 ml) was added triethylamine (0.102 ml, 0.730 mmol). The mixture was heated to 80° C. in a Microwave reactor for 50 min., cooled to r.t., purified by prep-HPLC to afford tert-butyl 4-(5-amino-2-cyano-4-nitrophenyl)piperazine-1-carboxylate (120 mg, 0.328 mmol, 44.9% yield). 1H-NMR (CD3OD, 500 MHz): δ 8.42 (1H, s), 6.45 (1H, s), 3.65-3.61 (4H, m), 3.28-3.25 (4H, m), 1.51 (9H, s). m/e (M+H): 348.3.

Workup

temperaturecooled to r.t.
custompurified by prep-HPLC

Sources & evidence

ORD record: ord-5667d1f6d7954aad9c8f0552851352bb
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362004B2

Reaction notes

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