Benzamidine → HCID 131722461, compound

HRID 1267155Notes

Reaction equation

HRID 1267155 reaction equation
[C:1]1(C2C=CC=CC=2)[C:2]([C:7]([CH2:9][CH2:10][C:11]2[C:16]3[NH:17][C:18](=[O:20])[O:19][C:15]=3[CH:14]=[C:13]([C:21]#[N:22])[CH:12]=2)=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.C(N)(=N)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)([O-])[O-].[NH4+:42].[NH4+]>>[C:5]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:4]=[CH:3][C:2]([C:7]([CH2:9][CH2:10][C:11]2[C:16]3[NH:17][C:18](=[O:20])[O:19][C:15]=3[CH:14]=[C:13]([C:21](=[NH:22])[NH2:42])[CH:12]=2)=[O:8])=[CH:1][CH:6]=1

Participants

4

Reactant 3

HCID 2332BenzamidineHCID 517111Ammonium CarbonateHCID 131722462HCID 131722462, compound

Product 1

HCID 131722461HCID 131722461, compound

Procedure

6-Cyanobenzoxazolinone (5.0 mmol, 0.80 g) was synthesized as previously described and added to a solution of 3-[1,1′]-biphenyl-1,2-propen-3-one (5.0 mmol, 1.04 g) and triethylamine (10.00 mmol, 1.39 mL) in 40 mL acetonitrile. The reaction mixture was warmed from ambient temperature to 77° C. for 2h. The reaction mixture was concentrated and placed under high vaccum to give the crude product. The crude material was used directly. LRMS: m/z 386 (M+NH4,100). The 1N-[[1,1′]-biphenylcarbonyl]ethyl-6-cyanobenzoxazolinone was converted to its corresponding benzamidine via the Pinner synthesis and amidination with ammonium carbonate to give crude 1N-[4-biphenylcarbonyl]ethyl-6-amidinobenzoxazolinone. The crude product was purified by standard reverse phase HPLC. LRMS: m/z 386(M+H,100). HRMS: calcd for C23H20N3O3, 386.150467; found, 386.150040.

Sources & evidence

ORD record
ord-870a33fbd31344b1b995ab3ff9f09aa1
Source dataset
uspto-grants-2003_04
Patent number
US06552042B2

Reaction notes

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