* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference:
[1] Archiv der Pharmazie (Weinheim, Germany), 1956, vol. 289, p. 651,660
2
[ 53710-18-2 ]
[ 10034-85-2 ]
[ 110-86-1 ]
[ 13472-80-5 ]
[ 7153-08-4 ]
Reference:
[1] Roczniki Chemii, 1938, vol. 18, p. 96,100[2] Chem. Zentralbl., 1939, vol. 110, # II, p. 643
3
[ 626-05-1 ]
[ 10034-85-2 ]
[ 110-86-1 ]
[ 13472-80-5 ]
[ 7153-08-4 ]
Reference:
[1] Roczniki Chemii, 1938, vol. 18, p. 96,100[2] Chem. Zentralbl., 1939, vol. 110, # II, p. 643
4
[ 108-96-3 ]
[ 7153-08-4 ]
Yield
Reaction Conditions
Operation in experiment
95%
With N-iodo-succinimide In acetonitrile for 3 h; Reflux
I Oa. 3,5-Diiodo-pyridin-4-ol Into a 3 L three necked round bottom flask I ,4-dihydropyridin-4-one (50.0 g, 0.50 mol) and N-iodosuccinimide (232 g, 1.00 mmol) were suspended inacetonitrile (1 L). The reaction mixture was refluxed for 3h. The mixture was cooled down with an ice bath and then filtered and washed with acetonitrile (150 mL). The light yellow solid was dried at 60°C under reduced pressure for 15 hr to obtain 165 g (95 percent) of the title compound as a light yellow solid. LC/MS (Method B): Rt 1.34 mm, (M+H) 348.
Reference:
[1] Patent: WO2015/144290, 2015, A1, . Location in patent: Page/Page column 69
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 3, p. 1078 - 1101
[3] DRP/DRBP Org.Chem., [4] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 20, p. 765
[5] Journal of the Society of Chemical Industry, London, 1943, vol. 62, p. 189
[6] Journal of the Society of Chemical Industry, London, 1946, vol. 65, p. 204
[7] Archiv der Pharmazie (Weinheim, Germany), 1956, vol. 289, p. 651,660
[8] Justus Liebigs Annalen der Chemie, 1932, vol. 494, p. 284,300
5
[ 626-64-2 ]
[ 7153-08-4 ]
Yield
Reaction Conditions
Operation in experiment
94%
With iodine; sodium acetate; sodium hydroxide In water for 0.333333 h; Reflux
To a solution of starting material 4-hydroxypyridine (9) (5.01 g, 52.6mmol, 1.0equiv) in H2O (67 mL) was added a solution of NaOH (13.2 g, 330mmol, 6.3 equiv) and NaOAc (40.1 g, 489mmol, 9.3 equiv) in H2O (167 mL). After the solution was stirred and refluxed,powdered I2 (46.9 g, 184mmol, 3.5 equiv) was added to the solution. The solution was then acidified with 50percent AcOH, and neutralized with 40percent NaOH. This acidification neutralization procedure was conducted under reflux and repeated three times in 20min. The forth acidification was made until free iodine was precipitated. After sublimation of the I2 by boiling, the residue was filtered, washed with boiling water, and then dried to give the product 12 as a colorless powder (17.18 g, 49.5mmol, 94percent); mp 280 °C with decomposition; IR (KBr, cm-1): 3166, 2952, 2880, 2805, 2360, 1605, 1525, 1334, 1270, 1038, 846, 746, 712, 597; 1HNMR (300 MHz, DMSO-d6): δ 11.95 (1H, s, OH), 8.27 (2H, s, H2/6); 13CNMR (75 MHz, DMSO-d6): δ 170.52, 143.04, 86.59; ESI-HRMS (m/z) calcd for C5H2I2NO [M-H]- 345.8231, found 345.8231.
Reference:
[1] Tetrahedron Letters, 1997, vol. 38, # 14, p. 2467 - 2470
[2] Chemical Communications, 2012, vol. 48, # 26, p. 3233 - 3235
[3] Bulletin of the Chemical Society of Japan, 2015, vol. 88, # 5, p. 673 - 683
[4] Journal of Materials Chemistry, 2001, vol. 11, # 9, p. 2271 - 2281
[5] Angewandte Chemie - International Edition, 2016, vol. 55, # 40, p. 12398 - 12402[6] Angew. Chem., 2016, vol. 128, # 40, p. 12586 - 12590,5
[7] Patent: US6642237, 2003, B1, . Location in patent: Page/Page column 79; 186
6
[ 108-96-3 ]
[ 89282-03-1 ]
[ 7153-08-4 ]
Reference:
[1] Archiv der Pharmazie (Weinheim, Germany), 1956, vol. 289, p. 651,660
With N-iodo-succinimide; In acetonitrile; for 3h;Reflux;
I Oa. 3,5-Diiodo-pyridin-4-ol Into a 3 L three necked round bottom flask I ,4-dihydropyridin-4-one (50.0 g, 0.50 mol) and N-iodosuccinimide (232 g, 1.00 mmol) were suspended inacetonitrile (1 L). The reaction mixture was refluxed for 3h. The mixture was cooled down with an ice bath and then filtered and washed with acetonitrile (150 mL). The light yellow solid was dried at 60C under reduced pressure for 15 hr to obtain 165 g (95 %) of the title compound as a light yellow solid. LC/MS (Method B): Rt 1.34 mm, (M+H) 348.
2-benzyl-5-{2-<i>tert</i>-butylcarbamoyl-4-[1-(7-iodo-furo[3,2-<i>c</i>]pyridin-2-yl)-1-methyl-ethyl]-piperazin-1-yl}-4-hydroxy-pentanoic acid[ No CAS ]
(S)-4-(1-Furo[3,2-c]pyridin-2-yl-1-methyl-ethyl)-1-[(2S,4R)-2-hydroxy-4-((3S,4S)-3-hydroxy-chroman-4-ylcarbamoyl)-5-phenyl-pentyl]-piperazine-2-carboxylic acid ethylamide[ No CAS ]
(S)-4-(1-Furo[3,2-c]pyridin-2-yl-1-methyl-ethyl)-1-[(2S,4R)-2-hydroxy-4-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-piperazine-2-carboxylic acid tert-butylamide[ No CAS ]
(S)-4-(1-Furo[3,2-c]pyridin-2-yl-1-methyl-ethyl)-1-[(2S,4R)-2-hydroxy-4-((3S,4S)-3-hydroxy-chroman-4-ylcarbamoyl)-5-phenyl-pentyl]-piperazine-2-carboxylic acid isobutyl-amide[ No CAS ]
(S)-4-(1-Furo[3,2-c]pyridin-2-yl-1-methyl-ethyl)-1-[(2S,4R)-2-hydroxy-4-((3S,4S)-3-hydroxy-chroman-4-ylcarbamoyl)-5-phenyl-pentyl]-piperazine-2-carboxylic acid tert-butylamide[ No CAS ]
(S)-1-[(2S,4R)-4-Benzyl-5-((3aS,9bS)-2,2-dimethyl-3a,9b-dihydro-4H-chromeno[4,3-d]oxazol-1-yl)-2-hydroxy-5-oxo-pentyl]-4-(1-furo[3,2-c]pyridin-2-yl-1-methyl-ethyl)-piperazine-2-carboxylic acid ethylamide[ No CAS ]
(S)-1-[(2S,4R)-4-Benzyl-5-((3aS,9bS)-2,2-dimethyl-3a,9b-dihydro-4H-chromeno[4,3-d]oxazol-1-yl)-2-hydroxy-5-oxo-pentyl]-4-(1-furo[3,2-c]pyridin-2-yl-1-methyl-ethyl)-piperazine-2-carboxylic acid isobutyl-amide[ No CAS ]
(S)-4-(1-Furo[3,2-c]pyridin-2-yl-1-methyl-ethyl)-1-[(2S,4R)-2-hydroxy-4-((3S,4S)-3-hydroxy-chroman-4-ylcarbamoyl)-5-phenyl-pentyl]-piperazine-2-carboxylic acid phenylamide[ No CAS ]
(S)-4-(1-Furo[3,2-c]pyridin-2-yl-1-methyl-ethyl)-1-[(2S,4R)-2-hydroxy-4-((3S,4S)-3-hydroxy-chroman-4-ylcarbamoyl)-5-phenyl-pentyl]-piperazine-2-carboxylic acid cyclopropylamide[ No CAS ]
1-[4-benzyl-5-(2,2-dimethyl-3a,9b-dihydro-4<i>H</i>-chromeno[4,3-<i>d</i>]oxazol-1-yl)-2-hydroxy-5-oxo-pentyl]-4-(1-furo[3,2-<i>c</i>]pyridin-2-yl-1-methyl-ethyl)-piperazine-2-carboxylic acid <i>tert</i>-butylamide[ No CAS ]
(S)-4-(1-Furo[3,2-c]pyridin-2-yl-1-methyl-ethyl)-1-[(2S,4R)-2-hydroxy-4-((3S,4S)-3-hydroxy-chroman-4-ylcarbamoyl)-5-phenyl-pentyl]-piperazine-2-carboxylic acid (2,2-dimethyl-propyl)-amide[ No CAS ]
(S)-1-[(2S,4R)-4-Benzyl-5-((3aS,9bS)-2,2-dimethyl-3a,9b-dihydro-4H-chromeno[4,3-d]oxazol-1-yl)-2-hydroxy-5-oxo-pentyl]-4-(1-furo[3,2-c]pyridin-2-yl-1-methyl-ethyl)-piperazine-2-carboxylic acid (2,2-dimethyl-propyl)-amide[ No CAS ]
(S)-1-[(2S,4R)-4-Benzyl-5-((3aS,9bS)-2,2-dimethyl-3a,9b-dihydro-4H-chromeno[4,3-d]oxazol-1-yl)-2-hydroxy-5-oxo-pentyl]-4-(1-furo[3,2-c]pyridin-2-yl-1-methyl-ethyl)-piperazine-2-carboxylic acid phenylamide[ No CAS ]
(S)-1-[(2S,4R)-4-Benzyl-5-((3aS,9bS)-2,2-dimethyl-3a,9b-dihydro-4H-chromeno[4,3-d]oxazol-1-yl)-2-hydroxy-5-oxo-pentyl]-4-(1-furo[3,2-c]pyridin-2-yl-1-methyl-ethyl)-piperazine-2-carboxylic acid cyclopropylamide[ No CAS ]
(S)-4-(1-Furo[3,2-c]pyridin-2-yl-1-methyl-ethyl)-1-[(2S,4R)-2-hydroxy-4-((3S,4S)-3-hydroxy-chroman-4-ylcarbamoyl)-5-phenyl-pentyl]-piperazine-2-carboxylic acid cyclopropylmethyl-amide[ No CAS ]
(S)-1-[(2S,4R)-4-Benzyl-5-((3aS,9bS)-2,2-dimethyl-3a,9b-dihydro-4H-chromeno[4,3-d]oxazol-1-yl)-2-hydroxy-5-oxo-pentyl]-4-(1-furo[3,2-c]pyridin-2-yl-1-methyl-ethyl)-piperazine-2-carboxylic acid (thiophen-2-ylmethyl)-amide[ No CAS ]
(S)-1-[(2S,4R)-4-Benzyl-5-((3aS,9bS)-2,2-dimethyl-3a,9b-dihydro-4H-chromeno[4,3-d]oxazol-1-yl)-2-hydroxy-5-oxo-pentyl]-4-(1-furo[3,2-c]pyridin-2-yl-1-methyl-ethyl)-piperazine-2-carboxylic acid cyclopropylmethyl-amide[ No CAS ]
(S)-4-(1-Furo[3,2-c]pyridin-2-yl-1-methyl-ethyl)-1-[(2S,4R)-2-hydroxy-4-((3S,4S)-3-hydroxy-chroman-4-ylcarbamoyl)-5-phenyl-pentyl]-piperazine-2-carboxylic acid (thiophen-2-ylmethyl)-amide[ No CAS ]
(S)-4-(1-Furo[3,2-c]pyridin-2-yl-1-methyl-ethyl)-1-[(2S,4R)-2-hydroxy-4-((3S,4S)-3-hydroxy-chroman-4-ylcarbamoyl)-5-phenyl-pentyl]-piperazine-2-carboxylic acid cyclopentylamide[ No CAS ]
(S)-4-(1-Furo[3,2-c]pyridin-2-yl-1-methyl-ethyl)-1-[(2S,4R)-2-hydroxy-4-((3S,4S)-3-hydroxy-chroman-4-ylcarbamoyl)-5-phenyl-pentyl]-piperazine-2-carboxylic acid benzylamide[ No CAS ]
(S)-1-[(2S,4R)-4-Benzyl-5-((3aS,9bS)-2,2-dimethyl-3a,9b-dihydro-4H-chromeno[4,3-d]oxazol-1-yl)-2-hydroxy-5-oxo-pentyl]-4-(1-furo[3,2-c]pyridin-2-yl-1-methyl-ethyl)-piperazine-2-carboxylic acid cyclopentylamide[ No CAS ]
(S)-1-[(2S,4R)-4-Benzyl-5-((3aS,9bS)-2,2-dimethyl-3a,9b-dihydro-4H-chromeno[4,3-d]oxazol-1-yl)-2-hydroxy-5-oxo-pentyl]-4-(1-furo[3,2-c]pyridin-2-yl-1-methyl-ethyl)-piperazine-2-carboxylic acid benzylamide[ No CAS ]
(αR,γS,2S)-N-((3S,4S)-3,4-dihydro-3-hydroxy-2H-1-benzopyran-4-yl)-4-(1-furo[3,2-c]pyridin-2-yl-1-methylethyl)-γ-hydroxy-α-(phenylmethyl)-2-[[(3,3,3-trifluoropropyl)amino]carbonyl]-1-piperazinepentanamide[ No CAS ]
1-[2-(<i>tert</i>-butyl-dimethyl-silanyloxy)-4-(2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-4-(1-furo[3,2-<i>c</i>]pyridin-2-yl-1-methyl-ethyl)-piperazine-2-carboxylic acid <i>tert</i>-butylamide[ No CAS ]
(αR,γS,2S)-N-((3S,4S)-3,4-dihydro-3-hydroxy-2H-1-benzopyran-4-yl)-4-(1-furo[3,2-c]pyridin-2-yl-1-methylethyl)-γ-hydroxy-2-[[(2,2,3,3,3-pentafluoropropyl)amino]carbonyl]-α-(phenylmethyl)-1-piperazinepentanamide[ No CAS ]