N-[3-[[4-(AMinoMethyl)benzoyl]aMino][1,1'-biphenyl]-4-yl]carbaMic Acid tert-Butyl Ester synthesis

11synthesis methods

Product Name:N-[3-[[4-(AMinoMethyl)benzoyl]aMino][1,1'-biphenyl]-4-yl]carbaMic Acid tert-Butyl Ester
CAS Number:1003316-12-8
Molecular formula:C25H27N3O3
Molecular Weight:417.5

1003316-11-7 Synthesis

N-[3-[[4-[(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl]benzoyl]amino][1,1'-biphenyl]-4-yl]carbamic Acid tert-Butyl Ester

1003316-11-7
9 suppliers
$625.00/25mg

N-[3-[[4-(AMinoMethyl)benzoyl]aMino][1,1'-biphenyl]-4-yl]carbaMic Acid tert-Butyl Ester

1003316-12-8
9 suppliers
$165.00/25mg

Yield:1003316-12-8 0.25 g

Reaction Conditions:

with hydrazine hydrate in ethanol at 80; for 1 h;

Steps:

tert-Butyl 3-(4-(aminomethyl)benzamido)biphenyl-4-ylcarbamate (6b).

Compound 5b (0.44 g, 1.00 mmol) and potassium phthalimide (0.37 g, 2.00 mmol) was added to N,N-dimethylformamide. The reaction mixture was stirred at 80 °C for 3h. The mixture was cooled down to r.t. and sat. aq. NH₄Cl (20 mL) was added the mixture. The precipitate was filtrated and washed with water (50 mL x 2) and dried by heating. The solid was then added to ethanol (20 mL), following the addition of hydrazine monohydrate (0.1 g, 2.00 mmol). The reaction mixture was allowed to stir at 80 °C for 1h before quenching with aq. HCl 2M (20 mL). The precipitate was filtrated and washed with water (50 mL x 2), then with dichloromethane (50 mL x 2). The solid was basified with NaOH 2M (20 mL) and extracted with ethyl acetate (50 mL) and brine (50 mL). The organic layer was washed with water (50 mL x 2), then dried over anhydrous Na₂SO₄ and concentrated to dryness to give compound 6b (0.25 g, 60%) as white solid. m.p. > 300 °C. ¹H NMR (400 MHz, CDCl₃) δ 9.28 (s, 1H), 8.02 (d, J = 2.0 Hz, 1H), 7.96 (d, J = 8.0 Hz, 2H), 7.57 (d, J = 7.2 Hz, 2H), 7.45-7.30 (m, 7H), 7.05 (s, 1H), 3.96 (s, 2H), 1.76 (br s, 2H), 1.53 (s, 9H). ¹³C NMR (100 MHz, CDCl₃) δ 165.6, 154.6, 147.1, 140.0, 138.9, 132.7, 131.1, 129.3, 128.7, 127.7, 127.3, 127.2, 127.0, 124.8, 124.5, 124.3, 81.4, 46.0, 28.3. HRMS (ESI) m/z (M+H)⁺ calcd for C₂₅H₂₈N₃O₃ = 418.2131; found 418.2134.

References:

La, Minh Thanh;Jeong, Byung-Hoon;Kim, Hee-Kwon [Bulletin of the Korean Chemical Society,2021,vol. 42,# 5,p. 740 - 743] Location in patent:supporting information

335255-33-9 Synthesis

N-(3-AMino[1,1'-biphenyl]-4-yl)-carbaMic Acid tert-Butyl Ester

335255-33-9
19 suppliers
$640.00/50mg

1003316-12-8
9 suppliers
$165.00/25mg

References

N-[3-[[4-(ChloroMethyl)benzoyl]aMino][1,1'-biphenyl]-4-yl]carbaMic Acid tert-Butyl Ester

1003316-10-6
8 suppliers
$675.00/50mg

1003316-12-8
9 suppliers
$165.00/25mg

References

876-08-4
264 suppliers
$11.00/25g

1003316-12-8
9 suppliers
$165.00/25mg

References

24424-99-5 Synthesis

24424-99-5
829 suppliers
$13.50/25G

1003316-12-8
9 suppliers
$165.00/25mg

References