Naphthalic anhydride → HCID 67531918, compound

HRID 1506815Notes

Reaction equation

HRID 1506815 reaction equation
Cl.[NH2:2][C:3]1[NH:7][C:6]2[CH:8]=[C:9]([NH:12][C:13]([C@@H]3C4(Cl)C(Cl)([Cl:22])C(Cl)(C(Cl)=C4Cl)[C@@H]3C(O)=O)=[O:14])[CH:10]=[CH:11][C:5]=2[N:4]=1.NC1C=CC2N=C(N(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)N(C(OC(C)(C)C)=O)C=2C=1.[C:63]1(=[O:77])[C:72]2[C:67]3[C:68](=[CH:73][CH:74]=[CH:75][C:66]=3C(=O)[O:64]1)[CH:69]=[CH:70][CH:71]=2>>[ClH:22].[NH2:2][C:3]1[NH:7][C:6]2[CH:8]=[C:9]([NH:12][C:13]([C:66]3[CH:75]=[CH:74][CH:73]=[C:68]4[C:67]=3[C:72]([C:63]([OH:77])=[O:64])=[CH:71][CH:70]=[CH:69]4)=[O:14])[CH:10]=[CH:11][C:5]=2[N:4]=1

Participants

4

Reactant 3

HCID 6693Naphthalic anhydrideHCID 67531620HCID 67531620, compoundHCID 86667328HCID 86667328, compound

Product 1

HCID 67531918HCID 67531918, compoundYield 96%

Procedure

Following the same procedure to synthesize (2S,3R)-3-(2-amino-1H-benzo[d]imidazol-6-ylcarbamoyl)-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-ene-2-carboxylic acid hydrochloride (10), tert-butyl 6-amino-2-(bis(tert-butoxycarbonyl)amino)-1H-benzo[d]imidazole-1-carboxylate (0.082 g, 183 mmol) was reacted with benzo[de]isochromene-1,3-dione (0.036 g, 0.183 mmol) to give the title compound (0.067 g, 96% yield) as a white solid. 1H NMR (400 MHz, DMSO) δ 11.43-11.21 (bs, 1H), δ 8.75 (s, 2H), δ 8.56 (q, 2H), δ 7.92 (t, 1H), δ 7.47 (s, 2H), δ 7.42 (d, 2H), δ 7.21 (d, 1H) ppm; 13C NMR (100 MHz, DMSO) δ 161.4, 151.9, 136.1, 133.2, 132.1, 130.9, 130.5, 129.4, 129.8, 129.3, 119.7, 119.3, 112.8, 106.9, 94.6 ppm; HRMS (ESI) Calcd for C19H14N4O3 (M+) 346.1066. Found 346.1061.

Sources & evidence

ORD record
ord-9f6b1971629f4b79a72d3403c22f8750
Source dataset
uspto-grants-2015_12
Patent number
US09221765B2

Reaction notes

Loading…