Diisopropylethylamine → HCID 59850135, compound

HRID 2064158Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6](F)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13].C(N(C(C)C)CC)(C)C.Cl.Cl.[O:27]1[CH2:32][CH2:31][CH:30]([N:33]2[CH2:38][CH2:37][CH:36]([NH2:39])[CH2:35][CH2:34]2)[CH2:29][CH2:28]1>CN(C)C=O>[Br:1][C:2]1[C:3]([C:12]([F:15])([F:14])[F:13])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH:39][CH:36]2[CH2:35][CH2:34][N:33]([CH:30]3[CH2:31][CH2:32][O:27][CH2:28][CH2:29]3)[CH2:38][CH2:37]2)[CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A stirred solution of 1-bromo-5-fluoro-4-nitro-2-(trifluoromethyl)benzene (D53) (0.30 g, 1.04 mmole) in dimethylformamide (5 ml) at room temperature under argon was treated with diisopropylethylamine (0.59 ml, 3.3 mmole) and 1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine dihydrochloride (D40) (0.28 g, 1.1 mmole) and heated at 70° C. for 1 hr. The mixture was concentrated under vacuum and the residue treated with 10% Na2CO3 solution and extracted with ethyl acetate. The extract was dried and concentrated under vacuum to leave an orange solid which was purified by chromatography on silica gel eluting with 0-20% methanol/ethyl acetate to afford the title compound as a bright yellow solid (0.38 g, 81%). MH+=452, 454.

Workup

concentrationThe mixture was concentrated under vacuum
additionthe residue treated with 10% Na2CO3 solution
extractionextracted with ethyl acetate
customThe extract was dried
concentrationconcentrated under vacuum
customto leave an orange solid which
customwas purified by chromatography on silica gel eluting with 0-20% methanol/ethyl acetate

Sources & evidence

ORD record: ord-ab8be07128c34d5abc1c47b8a127617f
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288412B2

Reaction notes

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