Trifluoroacetic acid → HCID 15434508, compound

HRID 1586040Notes

Reaction equation

HRID 1586040 reaction equation
ClC1C=CN=CC=1C=O.[C:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][O:21][C:22]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=1[C:30]1[C:35](/[CH:36]=[C:37](\[CH2:43][C:44]2[CH:49]=[C:48]3[O:50][CH2:51][O:52][C:47]3=[CH:46][C:45]=2[O:53][CH3:54])/[C:38]([O:40]CC)=[O:39])=[CH:34][CH:33]=[CH:32][N:31]=1)([O:12]C)=[O:11].CCCCCC.C(O)(C(F)(F)F)=O>C(O)C>[C:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][O:21][C:22]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=1[C:30]1[C:35](/[CH:36]=[C:37](\[CH2:43][C:44]2[CH:49]=[C:48]3[O:50][CH2:51][O:52][C:47]3=[CH:46][C:45]=2[O:53][CH3:54])/[C:38]([OH:40])=[O:39])=[CH:34][CH:33]=[CH:32][N:31]=1)([OH:12])=[O:11]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8058HexaneHCID 140466744-Chloropyridine-3-carbaldehydeHCID 86754427HCID 86754427, compound

Product 1

HCID 15434508HCID 15434508, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following the procedures in Example 4(b)-(c) except substituting 2-chloro-3-formyl-pyridine for 4chloro-3-formyl-pyridine and for the preparation of E-Ethyl 3-[2-[(2-Carbomethoxyphenyl)methoxy-4-methoxyphenyl]-pyridin-3-yl]-2-[2-methoxy4,5-methylenedioxybenzyl]prop-2-enoate shown in Example 6 (b), the title compound was prepared as a tan solid. (58 mg, 10% ) (400 MHz, CDCl3) δ 8.67 (d, J=3.5 Hz, 1H), 8.14 (d, J=7.8 Hz, 1H) 7.72 (s, 1H), 7.49-7.37 (m, 4H), 7.14 (dd, J=8.4 Hz, 4.8 Hz 1H), 6.71 (d, J=7.8 Hz, 1H), 6.70 (s, 1H), 6.48 (s, 1H), 6.43 (s, 1H), 5.85 (s, 2H), 5.49 (s, 2H), 3.89 (s, 3H), 3.71 (s, 3H), 2.87 (s, 2H); MS(ESP) m/e 570 [M+H]+ ; MS(ESN) m/e 568 [M-H]- ; mp 135-140°; Anal. (C32H27NO9.0.5H2O) calcd. C, 66.43; H, 4.88; N, 2.42: found. C, 66.47; H, 4.89; N, 2.40; HPLC tR 11.8 min, (Bakerbond Chiracel OC®; 25 cm×4.6 mm; hexane:ethanol, 80% with0.1%TFA;

Sources & evidence

ORD record
ord-1c20d88edfd042b1b5667e3ca333de9a
Source dataset
uspto-grants-1999_08
Patent number
US05942516

Reaction notes

Loading…