Acetonitrile → HCID 46899632, compound

To a solution of biphenyl-4-carboxylic acid (2.1 mmol) in dry CH2Cl2 (5.3 mL) and dry DMF (1 mL), kept at 0° C. under N2, was added oxalyl chloride (0.3 mL, 3.13 mmol). The mixture was reacted 20 min at 0° C. and 2 h at room temperature, then concentrated to give crude biphenyl-4-carbonyl chloride as a light-yellow solid. An amount of his sample (2 mmol) were dissolved in dry THF (20 mL) and the resulting solution added dropwise, at 0° C., to a suspension obtained by mixing 3 (1.3 mmol), Et3N (1.143 mL, 8.2 mmol) and dry THF (3 mL) at 0° C. under N2. The ensuing mixture was reacted at 0° C. for 30 min and at room temperature for 3 h, then evaporated. Purification by flash-chromatography (cyclohexane/EtOAc 1:1) and recrystallization gave pure URB894 as an ivory coloured solid. Yield 46%. Mp 218-220° C. (acetone/petroleum ether; sealed capillary tube; decomposition of the sample with changing of colour and shrinking of the mass was noted starting from 146° C.); [α]D20=−20° (c 0.55, CH3CN). MS (EI): m/z 267 (M+), 222, 181, 167 (100). IR (Nujol) 3270, 1827, 1641, 1540 cm−1; 1H NMR (d6-acetone) δ 4.53-4.65 (m, 2H), 4.50-4.59 (m, 1H), 7.38-7.55 (m, 3H), 7.70-7.84 (m, 4H), 8.00-8.07 (m, 2H), 8.68 (br d, 1H, J=7 Hz) ppm. 13C NMR (d6-acetone): δ 58.8, 65.1, 126.9, 127.0, 128.0, 128.1, 129.0, 131.9, 139.7, 144.4, 166.4, 169.2 ppm.

1. additionthe resulting solution added dropwise, at 0° C., to a suspension
2. customobtained
3. customThe ensuing mixture was reacted at 0° C. for 30 min and at room temperature for 3 h
4. customevaporated
5. customPurification
6. customby flash-chromatography (cyclohexane/EtOAc 1:1) and recrystallization
7. customgave pure URB894 as an ivory
8. customsealed capillary tube
9. customwas noted starting from 146° C.

ORD record

ord-f6475e5d9ed4439db6e851dd2008f791

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09321743B2