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Chemical Structure| 72179-84-1 Chemical Structure| 72179-84-1

Structure of 72179-84-1

Chemical Structure| 72179-84-1

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Product Details of [ 72179-84-1 ]

CAS No. :72179-84-1
Formula : CH6N2O2S
M.W : 110.14
SMILES Code : NS(=O)(NC)=O
MDL No. :MFCD02691960
InChI Key :NOXPGSDFQWSNSW-UHFFFAOYSA-N
Pubchem ID :13168287

Safety of [ 72179-84-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 72179-84-1 ]

* 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.

  • Downstream synthetic route of [ 72179-84-1 ]

[ 72179-84-1 ] Synthesis Path-Downstream   1~30

  • 1
  • [ 4047-86-3 ]
  • [ 72179-84-1 ]
  • 2
  • [ 74-89-5 ]
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  • [ 22398-14-7 ]
  • [ 72179-86-3 ]
  • 4
  • [ 10438-96-7 ]
  • [ 72179-84-1 ]
  • 5
  • [ 50-00-0 ]
  • [ 72179-84-1 ]
  • 2,6-Dimethyl-perhydro-1,5,2,4,6,8-dithiatetrazocin-1,1,5,5-tetroxid [ No CAS ]
  • 6
  • [ 50-00-0 ]
  • [ 72179-84-1 ]
  • 3,7-Dimethyl-2,6-dithia-1,3,5,7-tetraazabicyclo<3.3.1>nonan-2,2,6,6-tetroxide [ No CAS ]
  • 7
  • [ 72179-84-1 ]
  • [ 143130-92-1 ]
  • [ 93252-73-4 ]
  • [ 93252-72-3 ]
  • 8
  • [ 72179-84-1 ]
  • [ 129595-39-7 ]
  • C11H15N7O3S2 [ No CAS ]
  • 9
  • [ 72179-84-1 ]
  • [ 1670-46-8 ]
  • 3,4-dimethyl-3,5,6,7-tetrahydrocyclopenta<c><1,2,6>thiadiazine 2,2-dioxide [ No CAS ]
  • 1,4-dimethyl-1,5,6,7-tetrahydrocyclopenta<c><1,2,6>thiadiazine 2,2-dioxide [ No CAS ]
  • 10
  • [ 72179-84-1 ]
  • [ 874-23-7 ]
  • 1,4-dimethyl-5,6,7,8-tetrahydro-1H-2,1,3-benzothiadiazine 2,2-dioxide [ No CAS ]
  • 3,4-dimethyl-5,6,7,8-tetrahydro-3H-2,1,3-benzothiadiazine 2,2-dioxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.36 g (47.4%) Example 10 Preparation of N-methylsulfamide A solution of S-chlorosulfonamide (3.00 g, 0.0260 mol) in tetrahydrofuran (10 ml) was added dropwise to methylamine (40 ml, 2M in tetrahydrofuran) at 10 C. The resulting mixture was stirred one hour at 0 C. and three days at room temperature. The suspension was filtered and the filtrate concentrated under reduced pressure to give a yellow solid. Chromatography on silica gel (9:1 methylene chloride - methanol) afforded the title compound as an off-white solid, which was identified by NMR and mass spectral analysis. Yield: 1.36 g (47.4%).
  • 12
  • C31H31N3O4 [ No CAS ]
  • [ 72179-84-1 ]
  • [ 1033906-16-9 ]
YieldReaction ConditionsOperation in experiment
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 60℃; Cycloprop[d]indolo[2,1]-a][2]benzazepine-1a(2H)-carboxylic acid, 8-cyclohexyl-1,12b-dihydro-11-methoxy-5-[[[(methylamino)sulfonyl]amino]carbonyl]-, methyl ester. A solution of 8-Cyclohexyl-1,1a,2,12b-tetrahydro-11-methoxy-1a-(methoxycarbonyl)-cycloprop[d]indolo[2,1-a][2]benzazepine-5-carboxylic acid (140 mg, 0.31 mmol) and CDI (64 mg, 0.40 mmol) in THF (3 mL) was stirred for 1 hr at 60 C. <strong>[72179-84-1]N-<strong>[72179-84-1]methylsulfamide</strong></strong> (68 mg, 0.62 mmol) and DBU (71.6 mg, 0.47 mmol) were added and the mixture was stirred at 60 C. overnight. The reaction was then poured into cold water, acidified with dilute hydrochloric acid and extracted into ethyl acetate. The extracts were washed sequentially with dilute hydrochloric acid (0.1 N), and brine, and then dried (anhy. sodium sulfate), filtered and evaporated to provide the title compound as a brown solid. ESI-MS m/e 552 (MH+). This material was used without further purification.
  • 13
  • (+/-)-8-cyclohexyl-1,12b-dihydro-11-methoxy-cycloprop[d]indolo[2,1-a][2]benzazepine-1a,5(2H)-dicarboxylic acid 1a-methyl ester [ No CAS ]
  • [ 72179-84-1 ]
  • [ 1033906-16-9 ]
YieldReaction ConditionsOperation in experiment
Intermediate 22 Cycloprop[d]indolo[2,1-a][2]benzazepine-1a(2H)-carboxylic acid, 8-cyclohexyl-1,12b-dihydro-11-methoxy-5-[[[(methylamino)sulfonyl]amino]carbonyl]-, methyl ester. A solution of 8-Cyclohexyl-1,1a,2,12b-tetrahydro-11-methoxy-1a-(methoxycarbonyl)-cycloprop[d]indolo[2,1-a][2]benzazepine-5-carboxylic acid (140 mg, 0.31 mmol) and CDI (64 mg, 0.40 mmol) in THF (3 mL) was stirred for 1 hr at 60 C. <strong>[72179-84-1]N-<strong>[72179-84-1]methylsulfamide</strong></strong> (68 mg, 0.62 mmol) and DBU (71.6 mg, 0.47 mmol) were added and the mixture was stirred at 60 C. overnight. The reaction was then poured into cold water, acidified with dilute hydrochloric acid and extracted into ethyl acetate. The extracts were washed sequentially with dilute hydrochloric acid (0.1 N), and brine, and then dried (anhy. sodium sulfate), filtered and evaporated to provide the title compound as a brown solid. ESI-MS m/e 552 (MH+). This material was used without further purification.
  • 14
  • [ 72179-84-1 ]
  • [ 475287-14-0 ]
  • [ 1025765-26-7 ]
  • 15
  • [ 1033906-14-7 ]
  • [ 72179-84-1 ]
  • [ 1033906-16-9 ]
YieldReaction ConditionsOperation in experiment
Intermediate 22; Cycloprop fd] indolo [2, 1-aJ [2]benzazepine-la(2H)-carboxylic acid, 8- cyclohexyl-l,12b-dihydro-ll-methoxy-5-[[[(methylamino)sulfonyl] amino] carbonyl]- , methyl ester.; A solution of 8-Cyclohexyl-l,la,2,12b-tetrahydro-l l-methoxy-la- (methoxycarbonyl)-cycloprop[d]indolo[2,l-a][2]benzazepine-5-carboxylic acid (140 mg, 0.31 mmol) and CDI (64 mg, 0.40 mmol) in THF (3 mL) was stirred for 1 hr at 60 0C. <strong>[72179-84-1]N-<strong>[72179-84-1]methylsulfamide</strong></strong> (68 mg, 0.62 mmol) and DBU (71.6 mg, 0.47 mmol) <n="65"/>were added and the mixture was stirred at 60 0C overnight. The reaction was then poured into cold water, acidified with dilute hydrochloric acid and extracted into ethyl acetate. The extracts were washed sequentially with dilute hydrochloric acid (0.1 N), and brine, and then dried (anhy. sodium sulfate), filtered and evaporated to provide the title compound as a brown solid. ESI-MS m/e 552 (MH+). This material was used without further purification.
A solution of 8-Cyclohexyl-1,1a,2,12b-tetrahydro-11-methoxy-1a-(methoxycarbonyl)-cycloprop[d]indolo[2,1-a][2]benzazepine-5-carboxylic acid (140 mg, 0.31 mmol) and CDI (64 mg, 0.40 mmol) in THF (3 mL) was stirred for 1 hr at 60 C. <strong>[72179-84-1]N-<strong>[72179-84-1]methylsulfamide</strong></strong> (68 mg, 0.62 mmol) and DBU (71.6 mg, 0.47 mmol) were added and the mixture was stirred at 60 C. overnight. The reaction was then poured into cold water, acidified with dilute hydrochloric acid and extracted into ethyl acetate. The extracts were washed sequentially with dilute hydrochloric acid (0.1 N), and brine, and then dried (anhy. sodium sulfate), filtered and evaporated to provide the title compound as a brown solid. ESI-MS m/e 552 (MH+). This material was used without further purification.
Cyclaprop[d]indolo[2,1-a][2]benzazepine-1a(2H)-carboxylic acid, 8-cyclohexyl-1,12b-dihydro-11-methoxy-5-[[[(methylamino)sulfonyl]amino]carbonyl]-, methyl ester. A solution of 8-Cyclohexyl-1,1a,2,12b-tetrahydro-11-methoxy-1a-(methoxycarbonyl)-cycloprop[d]indolo[2,1-a][2]benzazepine-5-carboxylic acid (140 mg, 0.31 mmol) and CDI (64 mg, 0.40 mmol) in THF (3 mL) was stirred for 1 hr at 60 C. N-rnethylsulfamide (68 mg, 0.62 mmol) and DBU (71.6 mg, 0.47 mmol) were added and the mixture was stirred at 60 C. overnight. The reaction was then poured into cold water, acidified with dilute hydrochloric acid and extracted into ethyl acetate. The extracts were washed sequentially with dilute hydrochloric acid (0.1 N), and brine, and then dried (anhy. sodium sulfate), filtered and evaporated to provide the title compound as a brown solid. ESI-MS m/e 552 (MH+). This material was used without further purification.
A solution of 8-Cyclohexyl-1,1a,2,12b-tetrahydro-11-methoxy-1a-(methoxycarbonyl)-cycloprop[d]indolo[2,1-a][2]benzazepine-5-carboxylic acid (140 mg, 0.31 mmol) and CDI (64 mg, 0.40 mmol) in THF (3 mL) was stirred for 1 hr at 60 C. <strong>[72179-84-1]N-<strong>[72179-84-1]methylsulfamide</strong></strong> (68 mg, 0.62 mmol) and DBU (71.6 mg, 0.47 mmol) were added and the mixture was stirred at 60 C. overnight. The reaction was then poured into cold water, acidified with dilute hydrochloric acid and extracted into ethyl acetate. The extracts were washed sequentially with dilute hydrochloric acid (0.1 N), and brine, and then dried (anhy. sodium sulfate), filtered and evaporated to provide the title compound as a brown solid. ESI-MS m/e 552 (MH+). This material was used without further purification.
A solution of 8-Cyclohexyl-1,1a,2,12b-tetrahydro-11-methoxy-1a-(methoxycarbonyl)-cycloprop[d]indolo[2,1-a][2]benzazepine-5-carboxylic acid (140 mg, 0.31 mmol) and CDI (64 mg, 0.40 mmol) in THF (3 mL) was stirred for 1 hr at 60 C. <strong>[72179-84-1]N-<strong>[72179-84-1]methylsulfamide</strong></strong> (68 mg, 0.62 mmol) and DBU (71.6 mg, 0.47 mmol) were added and the mixture was stirred at 60 C. overnight. The reaction was then poured into cold water, acidified with dilute hydrochloric acid and extracted into ethyl acetate. The extracts were washed sequentially with dilute hydrochloric acid (0.1 N), and brine, and then dried (anhy. sodium sulfate), filtered and evaporated to provide the title compound as a brown solid. ESI-MS m/e 552 (MH+). This material was used without further purification.
A solution of 8-Cyclohexyl-1,1a,2,12b-tetrahydro-11-methoxy-1a-(methoxycarbonyl)-cycloprop[d]indolo[2,1-a][2]benzazepine-5-carboxylic acid (140 mg, 0.31 mmol) and CDI (64 mg, 0.40 mmol) in THF (3 mL) was stirred for 1 hr at 60 C. <strong>[72179-84-1]N-<strong>[72179-84-1]methylsulfamide</strong></strong> (68 mg, 0.62 mmol) and DBU (71.6 mg, 0.47 mmol) were added and the mixture was stirred at 60 C. overnight. The reaction was then poured into cold water, acidified with dilute hydrochloric acid and extracted into ethyl acetate. The extracts were washed sequentially with dilute hydrochloric acid (0.1 N), and brine, and then dried (anhy. sodium sulfate), filtered and evaporated to provide the title compound as a brown solid. ESI-MS m/e 552 (MH+). This material was used without further purification.
A solution of 8-Cyclohexyl-1,1a,2,12b-tetrahydro-11-methoxy-1a-(methoxycarbonyl)-cycloprop[d]indolo[2,1-a][2]benzazepine-5-carboxylic acid (140 mg, 0.31 mmol) and CDI (64 mg, 0.40 mmol) in THF (3 mL) was stirred for 1 hr at 60 C. <strong>[72179-84-1]N-<strong>[72179-84-1]methylsulfamide</strong></strong> (68 mg, 0.62 mmol) and DBU (71.6 mg, 0.47 mmol) were added and the mixture was stirred at 60 C. overnight. The reaction was then poured into cold water, acidified with dilute hydrochloric acid and extracted into ethyl acetate. The extracts were washed sequentially with dilute hydrochloric acid (0.1 N), and brine, and then dried (anhy. sodium sulfate), filtered and evaporated to provide the title compound as a brown solid. ESI-MS m/e 552 (MH+). This material was used without further purification.

  • 16
  • [ 108-86-1 ]
  • [ 72179-84-1 ]
  • [ 201230-82-2 ]
  • [ 1211973-93-1 ]
  • 17
  • [ 72179-84-1 ]
  • [ 201230-82-2 ]
  • [ 623-00-7 ]
  • [ 1211973-94-2 ]
  • 18
  • [ 108-86-1 ]
  • [ 72179-84-1 ]
  • [ 13939-06-5 ]
  • [ 1211973-93-1 ]
  • 19
  • [ 72179-84-1 ]
  • CH5N2O2S(1-)*K(1+) [ No CAS ]
  • 20
  • [ 72179-84-1 ]
  • [ 104-88-1 ]
  • [ 1438244-01-9 ]
YieldReaction ConditionsOperation in experiment
67% With titanium(IV) tetraethanolate; In tetrahydrofuran; for 7h;Reflux; General procedure: N-Alkylsulfamide 7 (3.63mmol, 1equiv) was added to a stirred solution of arylaldehyde (4.00mmol, 1.1equiv) and Ti(OEt)4 (1.95g, 7.26mmol, 2equiv) in THF (10mL). The solution was stirred at reflux for 7h, allowed to cool and then poured into stirred brine (100mL), EtOAc (50mL) was added and the mixture was stirred vigorously. The mixture was then filtered through Celite and flushed with further EtOAc. The filtrate was separated and the aqueous layer was back extracted with EtOAc (50mL). The combined organic layers were washed with brine (50mL), dried (Na2SO4) and concentrated to a cream solid. Purification by column chromatography or trituration gave the products as colourless to cream solids (yellow for 9f).
  • 21
  • [ 72179-84-1 ]
  • [ 100-52-7 ]
  • [ 1438244-02-0 ]
YieldReaction ConditionsOperation in experiment
86% With titanium(IV) tetraethanolate; In tetrahydrofuran; for 7h;Reflux; General procedure: N-Alkylsulfamide 7 (3.63mmol, 1equiv) was added to a stirred solution of arylaldehyde (4.00mmol, 1.1equiv) and Ti(OEt)4 (1.95g, 7.26mmol, 2equiv) in THF (10mL). The solution was stirred at reflux for 7h, allowed to cool and then poured into stirred brine (100mL), EtOAc (50mL) was added and the mixture was stirred vigorously. The mixture was then filtered through Celite and flushed with further EtOAc. The filtrate was separated and the aqueous layer was back extracted with EtOAc (50mL). The combined organic layers were washed with brine (50mL), dried (Na2SO4) and concentrated to a cream solid. Purification by column chromatography or trituration gave the products as colourless to cream solids (yellow for 9f).
  • 22
  • [ 125987-94-2 ]
  • [ 72179-84-1 ]
YieldReaction ConditionsOperation in experiment
General procedure: Trifluoroacetic acid (240mmol) in CH2Cl2 (20mL) was added dropwise to a stirred suspension of N-alkylsulfamoylcarbamate 6 (80mmol) in CH2Cl2 (100mL) at 0C. The solution was stirred overnight and allowed to warm to ambient temperature. The solution was concentrated in vacuo and the residue was taken up in EtOAc (75mL), washed with sat. NaHCO3 solution (2×50mL), dried (Na2SO4) and concentrated to a colourless oil. Compound 7b required no purification. All other species were isolated by column chromatography (5% MeOH/CH2Cl2) as crystalline solids or pale oils with literature properties.14,15
  • 23
  • [ 72179-84-1 ]
  • 5-chloro-4-((2,2-dimethylchroman-7-yloxy)methyl)-2-fluorobenzoic acid [ No CAS ]
  • 5-chloro-4-[(2,2-dimethylchroman-7-yl)oxymethyl]-2-fluoro-N-(methylsulfamoyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 16h; A mixture of 5-chloro-4-((2,2-dimethylchroman-7-yloxy)methyl)-2-fluorobenzoic acid (50 mg, 0.14 mmol), methyl(sulfamoyl)amine (23 mg, 0.21 mmol), 1-ethyl-(3-dimethylamino-propyl)carbodiimide hydrochloride (40 mg, 0.21 mmol) and 4-dimethylaminopyridine (26 mg, 0.21 mmol) in DCM (20 mL) was stirred at room temperature for 16 hrs. The mixture was diluted with HCl (2.0 N, 20 mL) and extracted with EtOAc (50*3 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by reverse phase Combiflash (18%-25% MeCN in 0.5% NH4HCO3) to give target product (35.4 mg, 56%) as a pale yellow solid. LCMS (ESI) Method A: RT=5.78 min, m/z: 456.7 [M+H]; 1H-NMR (500 MHz, MeOH-d4,): delta 7.77 (d, J=6.0 Hz, 1H), 7.42 (d, J=10.5 Hz, 1H), 6.99 (d, J=8.5 Hz, 1H), 6.52 (dd, J=9.0, 2.5 Hz, 1H), 6.36 (d, J=2.5 Hz, 1H), 5.14 (s, 2H), 2.74 (t, J=6.5 Hz, 2H), 2.71 (s, 3H), 1.80 (t, J=6.5 Hz, 2H), 1.32 (s, 6H).
  • 24
  • [ 72179-84-1 ]
  • (1aR,12bS)-8-cyclohexyl-11-fluoro-1a-((3-methyl-3,8-diazabicyclo[3.2.1]oct-8-yl)carbonyl)-1,1a,2,12b-tetrahydrocyclopropa[d]indolo[2,1-a][2]benzazepine-5-carboxylic acid [ No CAS ]
  • C34H40FN5O4S [ No CAS ]
  • 25
  • [ 72179-84-1 ]
  • 3-[(3,5-dimethoxy-4-methylbenzoyl)(3-phenylpropyl)amino]propanoic acid [ No CAS ]
  • 3,5-dimethoxy-4-methyl-N-{3-[(methylsulfamoyl)amino]-3-oxopropyl}-N-(3-phenylpropyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
58.5% Example 67 (100 mg, 0.259 mmol) was dissolved in tetrahydrofuran (4 mL) and carbonyldiimidazole (63.1 mg, 0.389 mmol) was added. The mixture was heated to 60 C for 1 hour. More carbonyldiimidazole (63.1 mg, 0.3 89 mmol) was added, and the resultant solution was stirred at 60 C for 1 hour. The solution was cooled down to room temperature and was then added dropwise through a syringe to a solution of 1,8-diazabicyclo[5.4.0]undec-7-ene (0.117 mL 0.778 mmol, DBU) and <strong>[72179-84-1]N-methylsulfuric diamide</strong> (86 mg, 0.778 mmol) in 0.6 mL tetrahydrofuran. The resulting mixture was stirred at room temperature overnight. The mixture was acidified with 1 N HC1 to pH=6-7 and then extracted with ethyl acetate 3 times. The organic layers were combined and concentrated. The residue was diluted with methanol to give a solution which was purified by preparative HPLC (0.1% CF3CO2H in H20/CH3CN) and lyophilized to give the titled compound (72.5 mg, 0.152 mmol, 58.5% yield). ?H NMR (400 MHz, DMSO-d6) ppm 11.39 (s, 1H), 7.46 (q, J = 4.9, 4.5 Hz, 1H), 7.14 (dd, J = 56.8, 38.2 Hz, 5H), 6.50 (s, 2H), 3.74 (s, 6H), 3.67-3.58 (m, 1H), 3.46 (d, J = 19.0 Hz, 4H), 3.19 (s,1H), 2.60 (s, 3H), 2.40 (s, 2H), 1.98 (s, 3H), 1.82 (a, J = 16.8 Hz, 2H); LC-MS (ESI+) m/z 478.2 (M+H), RT = 1.9 19 minutes.
  • 26
  • [ 72179-84-1 ]
  • 5-[(3,5-dimethoxy-4-methylbenzoyl)(3-phenylpropyl)amino]pentanoic acid [ No CAS ]
  • 3,5-dimethoxy-4-methyl-N-{5-[(methylsulfamoyl)amino]-5-oxopentyl}-N-(3-phenylpropyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
61.3% Material from Example 70-Step 3 (59 mg, 0.143 mmol) was dissolved in tetrahydrofuran (4 mL), and carbonyldiimidazole (69.4 mg, 0.428 mmol) was added. The mixture was heated to 60 C for 40 minutes. Additional carbonyldiimidazole (69.4 mg, 0.428 mmol) was added with continued stirring for 1 hour. N-Methylsulfuric diamide (47.1 mg, 0.42 8 mmol) and 1,8- diazabicyclo[5.4.0]undec-7-ene (0.065 mL 0.428 mmol, DBU) were added after the mixture was cooled down to room temperature, and the solution was stirred overnight at room temperature. The solution was acidified with 1 N HC1 to pH=2-.3 and extracted with ethyl acetate twice. The organic layers were combined and concentrated to give a residue which was purified by preparative HPLC (neutral phase, H20/CH3CN) and lyophilized to give the titled compound (44.2 mg, 0.087 mmol, 61.3% yield). ?H NMR (400 MHz, DMSO-d6) ppm 11.06 (s, 1H), 7.40-6.91 (m, 6H), 6.49 (s, 2H),3.76 (s, 6H), 3.29 (s, 4H), 2.51 (s, 2H), 2.48 (dd, J = 2.1, 1.5 Hz, 3H), 2.23 (d, J = 7.7 Hz, 2H), 2.00 (s, 3H), 1.94- 1.76 (m, 2H), 1.52 (d, J = 8.7 Hz, 4H); LC-MS (ESI) m/z 506.2 (M+H), RT = 1.941minutes.
  • 27
  • [ 72179-84-1 ]
  • 5-[1-(4-methoxyphenyl)cyclopropane-1-carbonyl](3-phenylpropyl)amino}pentanoic acid [ No CAS ]
  • 1-(4-methoxyphenyl)-N-{5-[(methylsulfamoyl)amino]-5-oxopentyl}-N-(3-phenylpropyl)cyclopropane-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
57.1% Material from Example 73-Step 1 (40 mg, 0.098 mmol) was dissolved in tetrahydrofuran (5 mL) and 1,1?-carbonyldiimidazole (47.5 mg, 0.293 mmol) was added. The mixture was heated to 60 C for 1 hour, then 1,8-diazabicyclo[5.4.0]undec-7-ene (44.6 mg, 0.293 mmol) and Nmethylsulfuric diamide (32.3 mg, 0.293 mmol) were added followed by stirring at room temperature for 12 hours. The mixture was concentrated, and the residue was dissolved in CH3OH (1.3 mL) to which a couple of drops of acetic acid were added to adjust the pH to 6-7. The filtered solution was purified by preparative HPLC (0.1% CF3CO2H/H20/CH3CN) to give the titled compound (28 mg, 0.056 mmol, 57.1% yield). ?H NMR (400 MHz, DMSO-d6) ppm 11.25 (s, 1H), 7.42 -7.36 (m, 1H),7.33 - 7.08 (m, 4H), 7.06 - 6.96 (m, 2H), 6.86 (d, J = 7.6 Hz, 2H), 3.73 (s, 2H), 3.26 - 3.16 (m, 3H),2.46 (s, 2H), 2.32 - 2.20 (m, 2H), 2.09 (t, J = 7.2 Hz, 1H), 1.73 (s, OH), 1.43 (s, 2H), 1.34 (s, 1H), 1.30- 1.21 (m, 1H), 1.18 (s, 1H), 1.13 (s, 1H), 1.07 (s, 1H), 0.93 (s, 1H).
  • 28
  • [ 72179-84-1 ]
  • trans-4-[3-({3-[1-(4-chlorophenyl)-1H-pyrazole-4-carbonyl]-4,5,6,7-tetraHydro-1-benzothiophen-2-yl}carbamoyl)benzene-1-sulfonyl](ethyl)amino}cyclohexane-1-carboxylic acid [ No CAS ]
  • N-{3-[1-(4-chlorophenyl)-1H-pyrazole-4-carbonyl]-4,5,6,7-tetrahydro-1-benzothiophen-2-yl}-3-(ethyl{trans-4-[(methylsulfamoyl)carbamoyl]cyclohexyl}sulfamoyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
6 mg With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In chloroform; N,N-dimethyl-formamide; at 20 - 30℃; for 2h; trans-4 - [3 - ({3- [1- (4-chlorophenyl) -1 H-pyrazole-4-carbonyl]-4,5,6,7-tetrahydro-1-benzothiophen-2-yl} carbamoyl)Benzene-1-sulfonyl] (ethyl) amino} cyclohexane-1-carboxylic acid (20 mg)In chloroform (1.0 mL)(Sulfamoylamino) methane (6.3 mg),1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (13 mg),4-dimethylaminopyridine (8.4 mg),N, N-dimethylformamide (1.0 mL) was added,And the mixture was stirred at room temperature for 2 hours.The reaction solution was concentrated under reduced pressure, and the obtained residue was purified by preparative HPLC (LP mode) to give the title compound (6.0 mg) as a yellow solid.
  • 29
  • [ 72179-84-1 ]
  • 2-{2-[2-(N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino)ethoxy]-2-methylpropoxy}acetic acid [ No CAS ]
  • 2-{2-[2-(N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino)ethoxy]-2-methylpropoxy}-N-(methylaminosulfonyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 6h;Inert atmosphere; Under the protection of nitrogen, 2-{2-[2-(N-(5,6-Diphenylpyrazin-2-yl)-N-isopropylamino)ethoxy]-2-methylpropoxy}acetic acid (926 mg, 2.00 mmol), <strong>[72179-84-1]methylaminosulfonamide</strong> (220 mg, 2.00 mmol) and 2-(7-Oxobenzotriazole)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU) (1000 mg, 2.60 mmol) dissolved in 50 mL Anhydrous N,N-dimethylformamide was reacted at room temperature for 6 h. The reaction solution was poured into 1N EtOAc (50 mL) and extracted with dichloromethane (100 mL*3)The organic phase was washed with water (100 mL*2) and saturated brine (100 mL*2), dried over anhydrous MgSO4, filtered and evaporated.It is purified by chromatography on silica gel column and collected under reduced pressure.Drying in vacuo gave 810 mg of yellow solid 2-{2-[2-(N-(5,6-diphenylpyrazin-2-yl)-N-isopropylamino)ethoxy]-2-yl Propyloxy}-N-(methylaminosulfonyl)acetamide, purity: 99.4%, yield: 73.0%.
  • 30
  • [ 72179-84-1 ]
  • N-(2-(difluoromethoxy)-6-methylpyridin-3-yl)-3-(2-isopropylphenyl)azetidine-3-carboxamide [ No CAS ]
  • N-(2-(difluoromethoxy)-6-methylpyridin-3-yl)-3-(2-isopropylphenyl)-1-(N-methylsulfamoyl)azetidine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In 1,4-dioxane; at 100℃; for 18h;Inert atmosphere; General procedure: To a solution of Ex 3 (50 mg, 0.12 mmol) and TEA (51 uL, 0.36 mmol) in dioxane (2 mL) is added sulfamide (12 mg, 0.12 mmol). The reaction mixture is stirred at 100C for 18 h and is then evaporated. The crude compound is purified by prep. HPLC (Prep HPLC 2) to give the title compound Ex 15-5 as a white solid (35 mg, 63% yield).
 

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