Reaction #2329042

ord-669213711e004f6493d51356168b95c5

Reaction equation

CN1CCN(c2ccc3nc(-c4ccc5c(c4)NC(=C4C=CC(=O)C=C4)N5)[nH]c3c2)CC1
bisbenzimidazole
CC(C)(C)[Si](C)(C)N1C(=O)C(Br)=C(Br)C1=O
N-TBDMS-2,3-dibromomaleimide
CCCC[N+](CCCC)(CCCC)CCCC.[F-]
TBAF
→
O=C1C(Br)=C(Br)C(=O)N1Cc1ccccc1
N-benzyl-2,3-dibromomaleimide
CN1CCN(c2ccc3nc(-c4ccc5c(c4)NC(=C4C=CC(=O)C=C4)N5)[nH]c3c2)CC1
bisbenzimidazole

Reactants

—
( 3 )
CN1CCN(c2ccc3nc(-c4ccc5c(c4)NC(=C4C=CC(=O)C=C4)N5)[nH]c3c2)CC1
bisbenzimidazole
CC(C)(C)[Si](C)(C)N1C(=O)C(Br)=C(Br)C1=O
N-TBDMS-2,3-dibromomaleimide
CCCC[N+](CCCC)(CCCC)CCCC.[F-]
TBAF

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherto afford 3

Procedure

As depicted in Scheme I, bisbenzimidazolomaleimide (3) was synthesized in an economical fashion from readily available precursors in two steps by condensing deprotonated bisbenzimidazole (4) with N-TBDMS-2,3-dibromomaleimide (6a) followed by deprotection with TBAF to afford 3. Lactam 4 was obtained by condensing deprotonated bisbenzimidazole 5 with N-benzyl-2,3-dibromomaleimide 7, yielding 9, followed by a reduction and deprotection sequence, as shown in Scheme 1.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07671046B2uspto-grants-2010_03