Name: 107753-78-6|Cyclopentyl (3-(2-methoxy-4-((o-tolylsulfonyl)carbamoyl)benzyl)-1-methyl-1H-indol-5-yl)carbamate|99%
Brand: Ambeed
SKU: A769198
Price: 6.0 USD
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Rating: 98 (27 reviews)

1
[ 88-19-7 ]
[ 107754-20-1 ]
[ 107753-78-6 ]

Yield	Reaction Conditions	Operation in experiment
86%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 25 - 35℃;
69%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 18h;
18%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 18h;	1.8 3-[2-Methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-1-methyl-1H-indol-5-yl)carbamic acid cyclopentyl ester: Under a nitrogen atmosphere, a mixture of 4-(5-cyclolpentyloxycarbonylamino-1-methyl-1H-indol-3-ylmethyl)-3-methoxy-benzoic acid (800 mg, 1.9 mmol), toluene-2-sulfonamide (341 mg, 2 mmol), 4-(dimethylamino)pyridine (244 mg, 2 mmol), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (384 mg, 2 mmol) was dissolved in dichloromethane (30 mL). The mixture was stirred at ambient temperature for about 18 hours, and then poured into 1 M hydrochloric acid (100 mL). Following standard extractive workup with chloroform, the crude product was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=2/1, v/v, elution) to afford the title compound (200 mg, 18%). 1H NMR (300 MHz, CDCl3) δ 8.62 (s, 1H), 8.29 (d, 1H, J=8.1 Hz), 7.55-7.22 (m, 9H), 6.81 (s, 1H), 6.50 (s, 1H), 5.23 (s, 1H), 4.08 (s, 2H), 3.91 (s, 3H), 3.75 (s, 3H), 2.71 (s, 3H), 1.96-1.76 (m, 8H); LC-MS: m/z=576 (MH)+; HPLC: 99% (Purity).

With dmap; dicyclohexyl-carbodiimide In methanol; dichloromethane at 30℃; for 4h;

9 Preparation Zafirlukast Acetonitrile Solvate (Formula IA) {3-[2-methoxy-4-carboxy-benzyl]-1-methyl-1H-indol-5-yl}-carbamic acid cyclopentyl ester (7 kg), dimethyl amino pyridine (2.5 kg), dicyclohexyl carbodiimide (3.9 kg), and dichloromethane (70 L) are charged and stirred for about 15 minutes. O-toluene sulphonamide (3.4 kg) is added at 30° C. and the reaction solution is stirred for about 4 hours at 30° C. The unwanted separated solid is filtered and the reaction solution is washed with dichloromethane (2×12 L). The obtained organic layer is washed with dilute hydrochloric acid and water and separated. The obtained organic solution is distilled off completely under vacuum below 45° C. Acetonitrile (14 L) is added and distilled off completely under vacuum. The obtained crude is cooled to 30° C., acetonitrile (35 L) is added and heated to 85° C., and stirred for about 40 minutes. The resultant reaction solution is cooled to 35° C. and stirred for about 55 minutes. The separated solid is filtered, washed with acetonitrile (7 mL), and suction dried for about 30 minutes. The obtained wet compound is again charged into a reactor containing methanol (84 L), heated to about 60° C., and stirred for about 30 minutes. The reaction solution is cooled to 30° C. and stirred for about 50 minutes for solid separation. The obtained solid is filtered, washed with methanol (7 L), and suction dried for 30 minutes. The solid is dried under vacuum at 70° C. for about 4 hours to afford the title compound.HPLC Purity: 97.5%

Reference： [1]Location in patent: experimental part Goverdhan, Gilla; Reddy, Anumula Raghupathi; Sampath, Aalla; Srinivas, Kurella; Himabindu, Vurimidi; Reddy, Ghanta Mahesh [Organic Process Research and Development, 2009, vol. 13, # 1, p. 67 - 72]
[2]Matassa; Maduskuie Jr.; Shapiro; Hesp; Snyder; Aharony; Krell; Keith [Journal of Medicinal Chemistry, 1990, vol. 33, # 6, p. 1781 - 1790]
[3]Current Patent Assignee: TEVA PHARMACEUTICAL INDUSTRIES LTD. - US2009/191183, 2009, A1 Location in patent: Page/Page column 53
[4]Current Patent Assignee: DR REDDY'S LABORATORIES LIMITED - US2009/149662, 2009, A1 Location in patent: Page/Page column 9-10

2
[ 50715-28-1 ]
[ 107753-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 74 percent / N-methylmorpholine / CH₂Cl₂ / 2 h 2: 88 percent / LiOH monohydrate / methanol; tetrahydrofuran; H₂O / 20 h 3: 69 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 18 h

Reference： [1]Matassa; Maduskuie Jr.; Shapiro; Hesp; Snyder; Aharony; Krell; Keith [Journal of Medicinal Chemistry, 1990, vol. 33, # 6, p. 1781 - 1790]

3
[ 70264-94-7 ]
[ 107753-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 45 percent / silver(I) oxide / dioxane / 20 h / 60 °C 2: 1.) NaH / 1.) THF, 10 min, 2.) 30 min 3: 98 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 2 h / 2587.7 Torr 4: 74 percent / N-methylmorpholine / CH₂Cl₂ / 2 h 5: 88 percent / LiOH monohydrate / methanol; tetrahydrofuran; H₂O / 20 h 6: 69 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 18 h
	Multi-step reaction with 7 steps 1: silver carbonate / toluene 2: sodium hydroxide / tetrahydrofuran; water / 20 - 65 °C 3: hydrogenchloride / tetrahydrofuran; water / 35 - 50 °C / pH 1 - 2 4: thionyl chloride / N,N-dimethyl-formamide; dichloromethane / 3.33 h / 41 °C 5: N,N-dimethyl-formamide / 25 °C / Reflux 6: N,N-dimethyl-formamide; dichloromethane / 20 °C / Reflux 7: sodium hydroxide; palladium on activated charcoal; hydrogen

Reference： [1]Matassa; Maduskuie Jr.; Shapiro; Hesp; Snyder; Aharony; Krell; Keith [Journal of Medicinal Chemistry, 1990, vol. 33, # 6, p. 1781 - 1790]
[2]Ancell, Claire L.; Derrick, Ian; Moseley, Jonathan D.; Stott, Jeffery A. [Organic Process Research and Development, 2004, vol. 8, # 5, p. 808 - 813]

4
[ 107754-14-3 ]
[ 107753-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 74 percent / N-methylmorpholine / CH₂Cl₂ / 2 h 2: 88 percent / LiOH monohydrate / methanol; tetrahydrofuran; H₂O / 20 h 3: 69 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 18 h

Reference： [1]Matassa; Maduskuie Jr.; Shapiro; Hesp; Snyder; Aharony; Krell; Keith [Journal of Medicinal Chemistry, 1990, vol. 33, # 6, p. 1781 - 1790]

5
[ 107786-36-7 ]
[ 107753-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 1.) NaH / 1.) THF, 10 min, 2.) 30 min 2: 98 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 2 h / 2587.7 Torr 3: 74 percent / N-methylmorpholine / CH₂Cl₂ / 2 h 4: 88 percent / LiOH monohydrate / methanol; tetrahydrofuran; H₂O / 20 h 5: 69 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 18 h
	Multi-step reaction with 6 steps 1: sodium hydroxide / tetrahydrofuran; water / 20 - 65 °C 2: hydrogenchloride / tetrahydrofuran; water / 35 - 50 °C / pH 1 - 2 3: thionyl chloride / N,N-dimethyl-formamide; dichloromethane / 3.33 h / 41 °C 4: N,N-dimethyl-formamide / 25 °C / Reflux 5: N,N-dimethyl-formamide; dichloromethane / 20 °C / Reflux 6: sodium hydroxide; palladium on activated charcoal; hydrogen

Reference： [1]Matassa; Maduskuie Jr.; Shapiro; Hesp; Snyder; Aharony; Krell; Keith [Journal of Medicinal Chemistry, 1990, vol. 33, # 6, p. 1781 - 1790]
[2]Ancell, Claire L.; Derrick, Ian; Moseley, Jonathan D.; Stott, Jeffery A. [Organic Process Research and Development, 2004, vol. 8, # 5, p. 808 - 813]

6
[ 107754-15-4 ]
[ 107753-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 98 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 2 h / 2587.7 Torr 2: 74 percent / N-methylmorpholine / CH₂Cl₂ / 2 h 3: 88 percent / LiOH monohydrate / methanol; tetrahydrofuran; H₂O / 20 h 4: 69 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 18 h
	Multi-step reaction with 5 steps 1: hydrogenchloride / tetrahydrofuran; water / 35 - 50 °C / pH 1 - 2 2: thionyl chloride / N,N-dimethyl-formamide; dichloromethane / 3.33 h / 41 °C 3: N,N-dimethyl-formamide / 25 °C / Reflux 4: N,N-dimethyl-formamide; dichloromethane / 20 °C / Reflux 5: sodium hydroxide; palladium on activated charcoal; hydrogen

Reference： [1]Matassa; Maduskuie Jr.; Shapiro; Hesp; Snyder; Aharony; Krell; Keith [Journal of Medicinal Chemistry, 1990, vol. 33, # 6, p. 1781 - 1790]
[2]Ancell, Claire L.; Derrick, Ian; Moseley, Jonathan D.; Stott, Jeffery A. [Organic Process Research and Development, 2004, vol. 8, # 5, p. 808 - 813]

7
[ 107754-19-8 ]
[ 107753-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 88 percent / LiOH monohydrate / methanol; tetrahydrofuran; H₂O / 20 h 2: 69 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 18 h

Reference： [1]Matassa; Maduskuie Jr.; Shapiro; Hesp; Snyder; Aharony; Krell; Keith [Journal of Medicinal Chemistry, 1990, vol. 33, # 6, p. 1781 - 1790]

8
[ 6146-52-7 ]
[ 107753-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 45 percent / silver(I) oxide / dioxane / 20 h / 60 °C 2: 1.) NaH / 1.) THF, 10 min, 2.) 30 min 3: 98 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 2 h / 2587.7 Torr 4: 74 percent / N-methylmorpholine / CH₂Cl₂ / 2 h 5: 88 percent / LiOH monohydrate / methanol; tetrahydrofuran; H₂O / 20 h 6: 69 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 18 h
	Multi-step reaction with 7 steps 1: silver carbonate / toluene 2: sodium hydroxide / tetrahydrofuran; water / 20 - 65 °C 3: hydrogenchloride / tetrahydrofuran; water / 35 - 50 °C / pH 1 - 2 4: thionyl chloride / N,N-dimethyl-formamide; dichloromethane / 3.33 h / 41 °C 5: N,N-dimethyl-formamide / 25 °C / Reflux 6: N,N-dimethyl-formamide; dichloromethane / 20 °C / Reflux 7: sodium hydroxide; palladium on activated charcoal; hydrogen

Reference： [1]Matassa; Maduskuie Jr.; Shapiro; Hesp; Snyder; Aharony; Krell; Keith [Journal of Medicinal Chemistry, 1990, vol. 33, # 6, p. 1781 - 1790]
[2]Ancell, Claire L.; Derrick, Ian; Moseley, Jonathan D.; Stott, Jeffery A. [Organic Process Research and Development, 2004, vol. 8, # 5, p. 808 - 813]

Yield	Reaction Conditions	Operation in experiment
69%		105 N-[4-[5-(Cyclopentyloxycarbonyl)amino-1-methylindol-3-ylmethyl]-3-methoxybenzoyl]-2-methylbenzenesulphonamide EXAMPLE 105 N-[4-[5-(Cyclopentyloxycarbonyl)amino-1-methylindol-3-ylmethyl]-3-methoxybenzoyl]-2-methylbenzenesulphonamide Using a similar procedure to that describe in Example 57, except using ortho-toluenesulphonamide and the acid described in Example 9, the title compound was obtained in 69% yield, as a white solid, m.p. 138°-140° C.
69%		105 N-[4-[5-(Cyclopentyloxycarbonyl)amino-1-methylindol-3-ylmethyl]-3-methoxybenzoyl]-2-methylbenzenesulphonamide Example 105 N-[4-[5-(Cyclopentyloxycarbonyl)amino-1-methylindol-3-ylmethyl]-3-methoxybenzoyl]-2-methylbenzenesulphonamide Using a similar procedure to that described in Example 57 , except using ortho-toluenesulphonamide and the acid described in Example 9 , the title compound was obtained in 69% yield, as a white solid, m.p. 138-140°C. Analysis calculated for:

10
[ 107753-78-6 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
84%	In tetrahydrofuran; water	111 Calcium N-[4-[5-(cyclopentyloxycarbonyl)amino-1-methylindol-3-ylmethyl]-3-methoxybenzoyl]-2-methylbenzenesulphonamide EXAMPLE 111 Calcium N-[4-[5-(cyclopentyloxycarbonyl)amino-1-methylindol-3-ylmethyl]-3-methoxybenzoyl]-2-methylbenzenesulphonamide Calcium oxide (0.0487 g.), and distilled water (10 ml.) were added sequentially to a solution of N-[4-[5-(cyclopentyloxycarbonyl)amino-1-methylindol-3-ylmethyl]-3-methoxybenzoyl]-2-methylbenzenesulphonamide (1.0 g.) in tetrahydrofuran (THF), (8 ml.). The turbid solution was heated at 50° C. for 20-25 minutes, and the cooled, clear, two-phase mixture evaporated (at about 50° C.). The residue was redissolved in THF (20 ml.), the solution filtered through a pad of diatomaceous earth, washing the filter cake with a little THF, the filtrate added dropwise to stirred ether (175 ml.), and the resulting solution added dropwise to stirred ether (300 ml.). The precipitate was collected by filtration. The filtrate was evaporated, redissolved in THF (3.5 ml.) and added dropwise to stirred ether (150 ml.). The precipitate was collected, combined with the first precipitate and dried to give the title compound (0.865 g., 84%) as a white solid, and a partial hydrate, m.p. 220° C. (approximately). Analysis calculated for: C62 H64 N6 O12 S2 Ca.0.75H2 O: C, 61.91: H, 5.49: N, 6.99, Found: C, 61.83; H, 5.49; N, 6.87.
84%	In tetrahydrofuran; water	111 Calcium N-[4-[5-(cyclopentyloxycarbonyl)amino-1-methylindol-3-ylmethyl]-3-methoxybenzoyl]-2-methylbenzenesulphonamide Example 111 Calcium N-[4-[5-(cyclopentyloxycarbonyl)amino-1-methylindol-3-ylmethyl]-3-methoxybenzoyl]-2-methylbenzenesulphonamide Calcium oxide (0.0487 g.), and distilled water (10 ml.) were added sequentially to a solution of N-[4-[5-(cyclopentyloxycarbonyl)amino-1-methylindol-3-ylmethyl]-3-methoxybenzoyl]-2-methylbenzenesulphonamide (1.0 g.) in tetrahydrofuran (THF), (8 ml.). The turbid solution was heated at 50°C for 20-25 minutes, and the cooled, clear, two-phase mixture evaporated (at about 50°C). The residue was redissolved in THF (20 ml.), the solution filtered through a pad of diatomaceous earth, washing the filter cake with a little THF, the filtrate added dropwise to stirred ether (175 ml.), and the resulting solution added dropwise to stirred ether (300 ml.). The precipitate was collected by filtration. The filtrate was evaporated, redissolved in THF (3.5 ml.) and added dropwise to stirred ether (150 ml.). The precipitate was collected, combined with the first precipitate and dried to give the title compound (0.865 g., 84%) as a white solid, and a partial hydrate, m.p. 220°C (approximately). Analysis calculated for

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - US4859692, 1989, A
[2]Current Patent Assignee: ASTRAZENECA PLC - EP199543, 1991, B1

11
[ 107753-78-6 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With potassium <i>tert</i>-butylate In tetrahydrofuran; methanol	1 A solution of zafirlukast potassium salt was prepared by adding potassium tert-butoxide (1.0 M in THF; 0.30 mL; 0.30 mmol) to a suspension of zafirlukast (156 mg; 0.272 mmol) in methanol (8.0 mL). An aliquot (1.05 mL, 20.5 mg zafirlukast potassium salt) was removed and evaporated to an oil in a separate vial. To the oil was added toluene (2.0 mL) followed by 2-butanol (0.2 mL). Crystals formed within minutes and were allowed to sit overnight with slow evaporation of the solvent. The solid was then collected and isolated via filtration. Amorphous solid was obtained from crystallization attempts in pure toluene. Crystals were obtained with various toluene/2-butanol mixtures as well as toluene/1-butanol and toluene/isopropanol mixtures.
	With potassium hydroxide In methanol at 50℃;	1 Another preparation was also utilized for the synthesis of zafirlukast potassium salt. To a suspension of zafirlukast (150 mg; 0.260 mmol) in methanol (3.0 mL) was added a solution of potassium hydroxide (15.6 mg; 0.278 mmol) in methanol (4.0 mL). The mixture was heated to 50 degrees C. and sonicated to dissolve the drug. The solution was then filtered through a 0.2 micrometer PTFE syringe filter and was allowed to sit overnight after a seed crystal was added. Some solid had crystallized overnight and the mixture was cooled to 0 degrees C. for 20 minutes to further crystallize the remaining drug. The solid was collected via filtration and washed with cold methanol (5.0 mL). The solid was then suspended in water and filtered. The solid was dried with flowing nitrogen gas for 1 hour and collected.

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - US2005/113410, 2005, A1 Location in patent: Page/Page column 10
[2]Current Patent Assignee: JOHNSON & JOHNSON INC - US2005/113410, 2005, A1 Location in patent: Page/Page column 10

12
[ 67-56-1 ]
[ 107753-78-6 ]
[ 847868-68-2 ]

Yield	Reaction Conditions	Operation in experiment
		2 The methanol solvate was prepared via recrystallization of the amorphous form from methanol followed by cold filtration. Zafirlukast methanol solvate was characterized by thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), powder x-ray diffraction (PXRD), and Raman spectroscopy

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - US2005/113410, 2005, A1 Location in patent: Page/Page column 10

13
[ 88-19-7 ]
[ CAS Unavailable ]
[ 107753-78-6 ]

Reference： [1]Location in patent: body text Goverdhan, Gilla; Reddy, Anumula Raghupathi; Sampath, Aalla; Srinivas, Kurella; Himabindu, Vurimidi; Reddy, Ghanta Mahesh [Organic Process Research and Development, 2009, vol. 13, # 1, p. 67 - 72]

14
[ 88-19-7 ]
[ 29906-67-0 ]
[ 50715-28-1 ]
[ 70264-94-7 ]
[ 1159195-67-1 ]
[ 1160235-24-4 ]
[ 1160235-26-6 ]
[ 107753-78-6 ]

Reference： [1]Organic Process Research and Development,2009,vol. 13,p. 67 - 72

15
[ 29906-67-0 ]
[ 107753-78-6 ]

Reference： [1]Synthetic Communications,2013,vol. 43,p. 498 - 504

16
[ 1414930-94-1 ]
[ 107753-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 2,2'-azobis(isobutyronitrile); 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / chloroform / 60 - 65 °C 2: silver(l) oxide / 1,4-dioxane / 20 - 100 °C

Reference： [1]Goverdhan, Gilla; Reddy, Anumula Raghupathi; Himabindu, Vurimidi; Reddy, Ghanta Mahesh [Synthetic Communications, 2013, vol. 43, # 4, p. 498 - 504]

17
[ 88-19-7 ]
[ 107753-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 25 - 35 °C 2: 2,2'-azobis(isobutyronitrile); 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / chloroform / 60 - 65 °C 3: silver(l) oxide / 1,4-dioxane / 20 - 100 °C

Reference： [1]Goverdhan, Gilla; Reddy, Anumula Raghupathi; Himabindu, Vurimidi; Reddy, Ghanta Mahesh [Synthetic Communications, 2013, vol. 43, # 4, p. 498 - 504]

18
[ 7151-68-0 ]
[ 107753-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 25 - 35 °C 2: 2,2'-azobis(isobutyronitrile); 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / chloroform / 60 - 65 °C 3: silver(l) oxide / 1,4-dioxane / 20 - 100 °C
	Multi-step reaction with 5 steps 1: 2,2'-azobis(isobutyronitrile); 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / chloroform / 4 h / Reflux 2: zinc dibromide / 1,4-dioxane / 14 h / 60 - 65 °C 3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 5 h / Reflux 4: hydrogen / tetrahydrofuran / 2 h / 25 - 35 °C 5: 4-methyl-morpholine / dichloromethane / 0.5 h / 25 - 35 °C / Inert atmosphere

Reference： [1]Goverdhan, Gilla; Reddy, Anumula Raghupathi; Himabindu, Vurimidi; Reddy, Ghanta Mahesh [Synthetic Communications, 2013, vol. 43, # 4, p. 498 - 504]
[2]Srinivas, Keesari; Srinivasan, Neti; Krishna, Muddasani Rama; Reddy, Chinta Raveendra; Arunagiri, Muthulingam; Lalitha, Routhu; Reddy, Kikkura Sri Rami; Reddy, Bijjula Sreenivasa; Reddy, Ghanta Mahesh; Reddy, Padi Pratap; Kumar, Muppa Kishore; Reddy, Manne Satyanaraya [Organic Process Research and Development, 2004, vol. 8, # 6, p. 952 - 954]

19
[ 107753-87-7 ]
[ 1414930-95-2 ]
[ 107753-78-6 ]

Yield	Reaction Conditions	Operation in experiment
8.9 g	With silver(l) oxide In 1,4-dioxane at 20 - 100℃;

Reference： [1]Goverdhan, Gilla; Reddy, Anumula Raghupathi; Himabindu, Vurimidi; Reddy, Ghanta Mahesh [Synthetic Communications, 2013, vol. 43, # 4, p. 498 - 504]

20
[ 143052-96-4 ]
[ 50715-28-1 ]
[ 107753-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: C₂₅H₂₃N₃O₆S*C₇H₁₀N₂ With palladium on activated charcoal; hydrogen; sodium hydroxide Stage #2: cyclopentyl chloroformate

Reference： [1]Ancell, Claire L.; Derrick, Ian; Moseley, Jonathan D.; Stott, Jeffery A. [Organic Process Research and Development, 2004, vol. 8, # 5, p. 808 - 813]

21
[ 138681-67-1 ]
[ 107753-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: thionyl chloride / N,N-dimethyl-formamide; dichloromethane / 3.33 h / 41 °C 2: N,N-dimethyl-formamide / 25 °C / Reflux 3: N,N-dimethyl-formamide; dichloromethane / 20 °C / Reflux 4: sodium hydroxide; palladium on activated charcoal; hydrogen
	Multi-step reaction with 3 steps 1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 5 h / Reflux 2: hydrogen / tetrahydrofuran / 2 h / 25 - 35 °C 3: 4-methyl-morpholine / dichloromethane / 0.5 h / 25 - 35 °C / Inert atmosphere

Reference： [1]Ancell, Claire L.; Derrick, Ian; Moseley, Jonathan D.; Stott, Jeffery A. [Organic Process Research and Development, 2004, vol. 8, # 5, p. 808 - 813]
[2]Srinivas, Keesari; Srinivasan, Neti; Krishna, Muddasani Rama; Reddy, Chinta Raveendra; Arunagiri, Muthulingam; Lalitha, Routhu; Reddy, Kikkura Sri Rami; Reddy, Bijjula Sreenivasa; Reddy, Ghanta Mahesh; Reddy, Padi Pratap; Kumar, Muppa Kishore; Reddy, Manne Satyanaraya [Organic Process Research and Development, 2004, vol. 8, # 6, p. 952 - 954]

22
[ 143052-94-2 ]
[ 107753-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 25 °C / Reflux 2: N,N-dimethyl-formamide; dichloromethane / 20 °C / Reflux 3: sodium hydroxide; palladium on activated charcoal; hydrogen

Reference： [1]Ancell, Claire L.; Derrick, Ian; Moseley, Jonathan D.; Stott, Jeffery A. [Organic Process Research and Development, 2004, vol. 8, # 5, p. 808 - 813]

23
[ 219583-10-5 ]
[ 50715-28-1 ]
[ 107753-78-6 ]

Yield	Reaction Conditions	Operation in experiment
89%	With 4-methyl-morpholine In dichloromethane at 25 - 35℃; for 0.5h; Inert atmosphere;

Reference： [1]Srinivas, Keesari; Srinivasan, Neti; Krishna, Muddasani Rama; Reddy, Chinta Raveendra; Arunagiri, Muthulingam; Lalitha, Routhu; Reddy, Kikkura Sri Rami; Reddy, Bijjula Sreenivasa; Reddy, Ghanta Mahesh; Reddy, Padi Pratap; Kumar, Muppa Kishore; Reddy, Manne Satyanaraya [Organic Process Research and Development, 2004, vol. 8, # 6, p. 952 - 954]

24
[ 118684-13-2 ]
[ 107753-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: zinc dibromide / 1,4-dioxane / 14 h / 60 - 65 °C 2: dmap; dicyclohexyl-carbodiimide / dichloromethane / 5 h / Reflux 3: hydrogen / tetrahydrofuran / 2 h / 25 - 35 °C 4: 4-methyl-morpholine / dichloromethane / 0.5 h / 25 - 35 °C / Inert atmosphere

Reference： [1]Srinivas, Keesari; Srinivasan, Neti; Krishna, Muddasani Rama; Reddy, Chinta Raveendra; Arunagiri, Muthulingam; Lalitha, Routhu; Reddy, Kikkura Sri Rami; Reddy, Bijjula Sreenivasa; Reddy, Ghanta Mahesh; Reddy, Padi Pratap; Kumar, Muppa Kishore; Reddy, Manne Satyanaraya [Organic Process Research and Development, 2004, vol. 8, # 6, p. 952 - 954]

25
[ CAS Unavailable ]
[ 107753-78-6 ]
[ 108-88-3 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol at 20℃; for 24h;

Reference： [1]Llinas, Antonio; Barbas, Rafael; Font-Bardia, Mercè; Quayle, Michael J.; Velaga, Sitaram; Prohens, Rafel [Crystal Growth and Design, 2015, vol. 15, # 8, p. 4162 - 4169]

26
[ CAS Unavailable ]
[ 107753-78-6 ]
[ 1801427-18-8 ]

Yield	Reaction Conditions	Operation in experiment
	In water at 20℃; for 24h;
	In ethanol at 20℃; for 71h;

Reference： [1]Llinas, Antonio; Barbas, Rafael; Font-Bardia, Mercè; Quayle, Michael J.; Velaga, Sitaram; Prohens, Rafel [Crystal Growth and Design, 2015, vol. 15, # 8, p. 4162 - 4169]
[2]Corner, Philip A.; Berry, David J.; McCabe, James F.; Barbas, Rafael; Prohens, Rafel; Du, Hongwen; Zhou, Hongyu; Llinas, Antonio [CrystEngComm, 2018, vol. 20, # 10, p. 1346 - 1351]

27
[ CAS Unavailable ]
[ 107753-78-6 ]
[ 1801427-18-8 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol at 20℃; for 24h;
	In acetonitrile at 20℃; for 64h;

Reference： [1]Llinas, Antonio; Barbas, Rafael; Font-Bardia, Mercè; Quayle, Michael J.; Velaga, Sitaram; Prohens, Rafel [Crystal Growth and Design, 2015, vol. 15, # 8, p. 4162 - 4169]
[2]Corner, Philip A.; Berry, David J.; McCabe, James F.; Barbas, Rafael; Prohens, Rafel; Du, Hongwen; Zhou, Hongyu; Llinas, Antonio [CrystEngComm, 2018, vol. 20, # 10, p. 1346 - 1351]

28
[ CAS Unavailable ]
[ 1801427-18-8 ]
[ 107753-78-6 ]
[ 1801427-18-8 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol at 20 - 60℃; for 96h;

Reference： [1]Llinas, Antonio; Barbas, Rafael; Font-Bardia, Mercè; Quayle, Michael J.; Velaga, Sitaram; Prohens, Rafel [Crystal Growth and Design, 2015, vol. 15, # 8, p. 4162 - 4169]

29
[ 107753-78-6 ]
[ CAS Unavailable ]
[ 1801427-16-6 ]

Yield	Reaction Conditions	Operation in experiment
	at 20 - 50℃; for 48h;

Reference： [1]Llinas, Antonio; Barbas, Rafael; Font-Bardia, Mercè; Quayle, Michael J.; Velaga, Sitaram; Prohens, Rafel [Crystal Growth and Design, 2015, vol. 15, # 8, p. 4162 - 4169]

30
[ 107753-78-6 ]
[ CAS Unavailable ]
[ 1801427-15-5 ]

Yield	Reaction Conditions	Operation in experiment
	at 20 - 80℃; for 48h;

Reference： [1]Llinas, Antonio; Barbas, Rafael; Font-Bardia, Mercè; Quayle, Michael J.; Velaga, Sitaram; Prohens, Rafel [Crystal Growth and Design, 2015, vol. 15, # 8, p. 4162 - 4169]

31
[ 3081-61-6 ]
[ 107753-78-6 ]
L-theanine zafirlukast [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water; isopropyl alcohol;	0.397 g of zafirlukast (0.690 mmol) and 0.122 g of L-<strong>[3081-61-6]theanine</strong> (0.700 mmol) were weighed directly into the bowl of an agate mortar, and wetted with 70% isopropanol to form a moderately thick slurry. The slurry was thoroughly ground at the time of mixing, and then periodically re-ground until the contents were dry. The XRPD pattern of the product is shown in Figure 31 a, while the FTIR spectrum is shown in Figure 31 b. The DSC melting endotherm of the product was characterized by a peak maximum at 21 1 C.

Reference： [1]Patent: WO2016/144590,2016,A1 .Location in patent: Paragraph 00163

32
[ 107753-78-6 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: ZAFIRLUKAST With palladium diacetate; trifluoroacetic acid at 40℃; for 2h; Sealed tube; Stage #2: With tritium; caesium carbonate; johnphos at 23℃; for 18h; Sealed tube;

Reference： [1]Yang, Haifeng; Dormer, Peter G.; Rivera, Nelo R.; Hoover, Andrew J. [Angewandte Chemie - International Edition, 2018, vol. 57, # 7, p. 1883 - 1887][Angew. Chem., 2018, vol. 130, # 7, p. 1901 - 1905,5]

33
[ 107753-78-6 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: ZAFIRLUKAST With palladium diacetate; trifluoroacetic acid at 40℃; for 2h; Sealed tube; Stage #2: With tritium; caesium carbonate; johnphos at 23℃; for 18h; Sealed tube;

Reference： [1]Yang, Haifeng; Dormer, Peter G.; Rivera, Nelo R.; Hoover, Andrew J. [Angewandte Chemie - International Edition, 2018, vol. 57, # 7, p. 1883 - 1887][Angew. Chem., 2018, vol. 130, # 7, p. 1901 - 1905,5]

34
[ CAS Unavailable ]
[ 107753-78-6 ]
[ 108-88-3 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	at 20℃; for 29h;

Reference： [1]Corner, Philip A.; Berry, David J.; McCabe, James F.; Barbas, Rafael; Prohens, Rafel; Du, Hongwen; Zhou, Hongyu; Llinas, Antonio [CrystEngComm, 2018, vol. 20, # 10, p. 1346 - 1351]

35
[ 2216756-14-6 ]
[ 107753-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: sodium persulfate / dimethyl sulfoxide / 5 h / 80 °C 2.1: 10% Pd/C; hydrogen; hydrogenchloride; water / methanol / 6 h 3.1: zinc(II) chloride; benzoic acid anhydride / dichloromethane / 0.17 h / 20 °C / Inert atmosphere 3.2: 2 h / 20 °C / Inert atmosphere 4.1: hydrogen / methanol / 2 h / 20 °C 4.2: 3 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH (IN) - WO2019/130334, 2019, A1

36
[ 1224640-22-5 ]
[ 107753-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / N,N-dimethyl-formamide / 2.5 h / 80 °C 2.1: sodium persulfate / dimethyl sulfoxide / 5 h / 80 °C 3.1: 10% Pd/C; hydrogen; hydrogenchloride; water / methanol / 6 h 4.1: zinc(II) chloride; benzoic acid anhydride / dichloromethane / 0.17 h / 20 °C / Inert atmosphere 4.2: 2 h / 20 °C / Inert atmosphere 5.1: hydrogen / methanol / 2 h / 20 °C 5.2: 3 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH (IN) - WO2019/130334, 2019, A1

37
[ 2216756-31-7 ]
[ 107753-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 10% Pd/C; hydrogen; hydrogenchloride; water / methanol / 6 h 2.1: zinc(II) chloride; benzoic acid anhydride / dichloromethane / 0.17 h / 20 °C / Inert atmosphere 2.2: 2 h / 20 °C / Inert atmosphere 3.1: hydrogen / methanol / 2 h / 20 °C 3.2: 3 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH (IN) - WO2019/130334, 2019, A1

38
N₁-{3-methoxy-4-(N-methyl-5-nitro-1H-3-indolyl)methylbenzoyl}-2-methyl-1-benzenesulfonamide [ No CAS ]
[ 50715-28-1 ]
[ 107753-78-6 ]

Yield	Reaction Conditions	Operation in experiment
89%		A solution of N-{3-methyl-4-[(N-methyl-5-nitro-lH-3-indolyl) methyl benzoyl }-2-methyl-1-benzenesulfonamide, compound of formula II (100 mg, 0.20 mmol) in MeOH (2 mL), and Raney-nickel (2 mg, 30 mol%) was placed under hydrogen pressure at room temperature for 2 h. The reaction mass was filtered through a celite bed, and the catalyst was washed with diethyl ether (2 x 10 mL). The combined filtrates were concentrated under reduced pressure and dried using height vacuo for 1 h. The obtained residue and N-methyl morphine (26 m , 0.24 mmol) in CH2Cl2 (2 ml) was slowly added <strong>[50715-28-1]cyclopentyl chloroformate</strong> (25 m, 0.20 mmol) at 0 C, and the resulting reaction mass was stirred at room temperature for 3 h. After completion of the reaction, the solvent was removed under reduced pressure and the solid precipitate was washed with water (5 ml) and extracted with CHCl3 (10 ml) and dried over sodium sulphate and evaporated in under reduced pressure. The crude compound was purified by column chromatography to afford title product compound of formula I (102 mg, 89%) as a pale yellow solid; Rf = 0.7 (silica, EtOAc: hexane = 4:6); IR (neat): 3476, 2951, 2925, 2850, 1723, 1689, 1554, 1499, 1431, 1270, 1163, 1062, 1036, 872, 758 cm-1; M.P. = 136-141 C; 1H NMR (500 MHz, CDCI3): d 9.18 (s, 1H), 8.26 (dd, / = 8.0, 1.3 Hz, 1H), 7.51 (td, 7 = 7.5, 1.3 Hz, 2H), 7.40 (t, 7 = 7.5 Hz, 1H), 7.31 (d, J = 1.5 Hz, 1H), 7.29 (d, / = 7.5 Hz, 1H), 7.19 (d, / = 8.6 Hz, 1H), 7.16 (dd, / = 7.9, 1.6 Hz, 1H), 7.09 (d, / = 7.9 Hz, 2H), 6.77 (s, 1H), 6.51 (s, 1H), 5.18 (ddd, J = 8.9, 5.9, 2.6 Hz, 1H), 4.03 (s, 2H), 3.85 (s, 3H), 3.70 (s, 3H), 2.68 (s, 3H), 1.86 (s, 2H), 1.74 (d, J = 12.6 Hz, 4H), 1.60 (s, 2H); 13C NMR (125 MHz, CDCl3): d 13C NMR (125 MHz, CDCl3) d 164.4, 158.0, 138.0, 137.0, 137.0, 134.4, 134.1, 133.0, 138.0, 130.1, 130.0, 128.4, 128.1, 127.0, 119.4, 115.2, 112.0, 110.0, 110.0, 56.0, 33.0, 33.0, 25.4, 24.0, 21.0; HRMS (m/z): [M + Na] + calcd. for C3IH33N306S+ 598.1988, found 598.1975.

Reference： [1]Patent: WO2019/130334,2019,A1 .Location in patent: Page/Page column 12; 13

39
[ 64230-23-5 ]
[ 107753-78-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / N,N-dimethyl-formamide / 2.5 h / 80 °C 2.1: sodium persulfate / dimethyl sulfoxide / 5 h / 80 °C 3.1: 10% Pd/C; hydrogen; hydrogenchloride; water / methanol / 6 h 4.1: zinc(II) chloride; benzoic acid anhydride / dichloromethane / 0.17 h / 20 °C / Inert atmosphere 4.2: 2 h / 20 °C / Inert atmosphere 5.1: hydrogen / methanol / 2 h / 20 °C 5.2: 3 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH (IN) - WO2019/130334, 2019, A1

40
[ 107753-78-6 ]
[ 2500901-01-7 ]

Yield	Reaction Conditions	Operation in experiment
42%	With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; deuterium In tetrahydrofuran at 55℃; for 22h; Inert atmosphere;

Reference： [1]Chaudret, Bruno; Daniel-Bertrand, Marion; Derdau, Volker; Fazzini, Pier-Francesco; Feuillastre, Sophie; Garcia-Argote, Sébastien; Mustieles Marin, Irene; Palazzolo, Alberto; Pieters, Grégory; Tricard, Simon [Angewandte Chemie - International Edition, 2020, vol. 59, # 47, p. 21114 - 21120][Angewandte Chemie, 2020, vol. 132, # 47, p. 21300 - 21306,7]

41
[ 2624101-88-6 ]
[ 2624101-87-5 ]
[ 107753-78-6 ]

Yield	Reaction Conditions	Operation in experiment
40%	With 1,10-Phenanthroline; (1,2-dimethoxyethane)dichloronickel(II); [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride In N,N-dimethyl acetamide at 20℃; for 16h; Irradiation;

Reference： [1]Kim, Weonjeong; Koo, Jangwoo; Lee, Hong Geun [Chemical Science, 2021, vol. 12, # 11, p. 4119 - 4125]

42
[ 107753-78-6 ]
[ 219583-10-5 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol for 48h;	2 The aniline derivative was prepared by dissolving zafirlukast in methanol with stirring. Acyl chloride was added to the mixture with stirring and was left to react for 48 hours.

Reference： [1]Current Patent Assignee: RIGSHOSPITALET - WO2021/69542, 2021, A1 Location in patent: Page/Page column 12

43
[ CAS Unavailable ]
[ 107753-78-6 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
33 %	With 1,8-Diaminonaphthalene In dichloromethane at 40℃;

Reference： [1]Huang, Wenxin; Wang, Jia-Xi; Shen, Xiaofei; Lei, Yuqin; Chen, Xueqin; Jia, Da; Zhang, Xia; Sun, Qingxiang [Journal of Medicinal Chemistry, 2023, vol. 66, # 2, p. 1574 - 1582]

44
[ 107753-78-6 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
35 %	With 1,8-Diaminonaphthalene In dichloromethane at 40℃;

Reference： [1]Huang, Wenxin; Wang, Jia-Xi; Shen, Xiaofei; Lei, Yuqin; Chen, Xueqin; Jia, Da; Zhang, Xia; Sun, Qingxiang [Journal of Medicinal Chemistry, 2023, vol. 66, # 2, p. 1574 - 1582]

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{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

CAS No. :	107753-78-6	MDL No. :	MFCD00864775
Formula :	C₃₁H₃₃N₃O₆S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YEEZWCHGZNKEEK-UHFFFAOYSA-N
M.W :	575.68	Pubchem ID :	5717
Synonyms :	ICI 204219	Chemical Name :	Cyclopentyl (3-(2-methoxy-4-((o-tolylsulfonyl)carbamoyl)benzyl)-1-methyl-1H-indol-5-yl)carbamate

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
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P233	Keep container tightly closed.
P234	Keep only in original container.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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H401	Toxic to aquatic life
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H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 107753-78-6 ] {[proInfo.proName]}

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[ 107753-78-6 ] Synthesis Path-Upstream 1~18

[ 107753-78-6 ] Synthesis Path-Downstream 1~44

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