94341-56-7|(4-(Phenylsulfonyl)phenyl)methanamine| Ambeed

CAS No. :	94341-56-7
Formula :	C₁₃H₁₃NO₂S
M.W :	247.31
SMILES Code :	NCC1=CC=C(S(=O)(C2=CC=CC=C2)=O)C=C1
MDL No. :	MFCD22392055
InChI Key :	MTVXOTIZNSJKIY-UHFFFAOYSA-N
Pubchem ID :	58775895

Safety of [ 94341-56-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P280-P305+P351+P338-P310

Application In Synthesis of [ 94341-56-7 ]

* 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 [ 94341-56-7 ]

[ 94341-56-7 ] Synthesis Path-Downstream 1~54

1
[ 94341-56-7 ]
N-(4-Benzenesulfonyl-benzyl)-4-methyl-benzenesulfonamide [ No CAS ]

References: [1]Chemistry Letters,1984,p. 1733 - 1736.

2
1-Azidomethyl-4-benzenesulfonyl-benzene [ No CAS ]
[ 94341-56-7 ]

References: [1]Chemistry Letters,1984,p. 1733 - 1736.

3
[ 98-10-2 ]
[ 94341-56-7 ]

References: [1]Journal of the Chemical Society,1948,p. 381.

4
[ 5361-54-6 ]
[ 94341-56-7 ]

References: [1]Journal of the Chemical Society,1948,p. 381.

5
[ 402925-20-6 ]
[ 94341-56-7 ]

References: [1]Chemical and pharmaceutical bulletin,1958,vol. 6,p. 415,417.
Chemical and Pharmaceutical Bulletin,1959,vol. 7,p. 734,735.

6
[ 71-43-2 ]
[ 94341-56-7 ]

References: [1]Chemical and pharmaceutical bulletin,1958,vol. 6,p. 415,417.
Chemical and Pharmaceutical Bulletin,1959,vol. 7,p. 734,735.

7
[ 904311-41-7 ]
[ 94341-56-7 ]
[ 904311-94-0 ]

Yield	Reaction Conditions	Operation in experiment
42%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; diisopropylamine;nickel; In N,N-dimethyl-formamide; at 20℃; for 20h;	4-Benzenesulfonyl-benzonitrile (100 mg, 0.41 mmol) and Raney Ni (70 mg, prewashed with methanol) was mixed in 30 mL of ammonia (20% solution in methanol). The heavy walled reaction vessel was charged with H2 (60 psi) and the reaction was shaken at room temperature for 10 h. The mixture was filtered to remove the catalyst, then the filtrate was concentrated to afford an oil (80 mg). To this oil, was added 4-amino-6-chloro-5-cyano-pyridine-2-carboxylic acid from Example 181 D (50 mg, 0.25 mmol) in 1 mL of anhydrous N,N-dimethylformamide, followed by O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium tetrafluoroborate (94 mg, 0.3 mmol), and N,N-diisopropylamine (52 muL, 0.3 mmol). The mixture was stirred at room temperature for 20 h. The crude product was purified via reverse phase HPLC (0-70% CH3CN in 10 mM aq. ammonium acetate) to provide 45 mg (42%) of titled compound as a white solid. 1H NMR (300 MHz, DMSO-d6) delta ppm 4.48 (d, J=6.4 Hz, 2H), 7.35 (s, 1H), 7.50 (d, J=8.5 Hz, 2H), 7.56-7.71 (m, 3H), 7.79 (s, 2H), 7.86-7.97 (m, 4H), 9.26 (t, J=6.3 Hz, 1H). MS (ESI+) m/e=427 (M+H)+.

References: [1]Patent: US2006/173050,2006,A1 .Location in patent: Page/Page column 75.

8
[ 1002-18-2 ]
[ 94341-56-7 ]
5-chloro-2-(4-benzenesulfonyl-benzyl)-isothiazol-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Compound 1b was then transferred via pipette to a second flask (cooled in an ice water bath) containing DCM (250 mL), 4-iodobenzylamine Compound 1c (5.50 grams, 0.024 mol) and TEA (3.3 mL, 0.024 mol). The reaction mixture was stirred for 3 hrs, then approximately 2 molar equivalents of sulfuryl chloride (4.00 mL, 0.050 mol) was added and the mixture was stirred at ambient temperature for an additional 3 hrs. The mixture was evaporated in vacuo and the resulting crude oil was dissolved in DCM (250 mL), washed with water, dried over magnesium sulfate and concentrated in vacuo. The crude product was chromatographed on a silica gel flash column using a mobile phase of hexane:EtOAc in a 2:1 ratio to afford the intermediate 4,5-dichloro-2-(4-iodo-benzyl)-isothiazol-3-one Compound 1d as a solid. M.P. 104.5-107 C.; 1H NMR (CDCl3) delta 7.71 (m, 2H), 7.07 (d, 2H), 4.89 (s, 2H). Using the procedure of Example 1 and Compound 16e in place of Compound 1c, Compound 38 was obtained. 1H NMR (CDCl3) delta 7.95 (d, 4H), 7.59-7.49 (m, 3H), 7.40 (m, 2H), 6.31 (s, 1H), 4.93 (s, 2H), MS 387.9 (M+H+).

References: [1]Patent: US2006/293374,2006,A1 .Location in patent: Page/Page column 15; 25.

9
[ 1194-02-1 ]
[ 873-55-2 ]
[ 94341-56-7 ]

References: [1]Patent: WO2012/31197,2012,A1 .

10
[ 1194-02-1 ]
[ 94341-56-7 ]

References: [1]Patent: WO2012/31199,2012,A1 .
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 4875 - 4885.
[3]Patent: WO2013/127268,2013,A1 .

11
[ 873-55-2 ]
[ 94341-56-7 ]

References: [1]Patent: WO2012/31199,2012,A1 .
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 4875 - 4885.
[3]Patent: WO2013/127268,2013,A1 .

12
[ 94341-56-7 ]
methyl N’-cyano-N-(pyridin-3-yl)carbamimidothioate [ No CAS ]
[ 1362752-16-6 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;dmap; In pyridine; at 60℃;	D: 2-cvano-l-(4-(phenylsulfonyl)benzyl)-3-(pyridin-3-yl)guanidine:To a solution of methyl N'-cyano-N-(pyridin-3-yl)carbamimidothioate (50 mg,0.26 mmol) and (4-[phenylsulfonyl] phenyl) methanamine ( 81 mg, 0266 mmol) in pyridine (3 mL) was added TEA (73 mu, 0.520 mmol) and DMAP (3.18 mg, 0.026 mmol). The resulting mixture was stirred overnight at 60 C. The reaction mixture was cooled and concentrated under vacuo to afford an off white solid. The crude material was purified by silica-gel chromatography (2%MeOH/DCM to6%MeOH/DCM) to afford the title compound.1H NMR (300 MHz, DMSO-d6) delta 8.45 (s, 1H), 8.37 (d, 1H), 7.90 (m, 5H), 7.63 (m, 5H), 7.52 (d, 2H), 7.36 (m, 1H), 4.45 (d, 2H)LC-MS (ESI): 389.9 (M-l).

References: [1]Patent: WO2012/31199,2012,A1 .Location in patent: Page/Page column 81.
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 337 - 343.
[3]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 337 - 343.

13
[ 1362754-90-2 ]
[ 94341-56-7 ]
[ 1362752-18-8 ]

Yield	Reaction Conditions	Operation in experiment
		B: 2-cvano-l-(imidazo[l,2-alpyridin-7-yl)-3-(4-(phenylsulfonyl)benzyl)guanidine:In a 50 mL round-bottomed flask was added (Z)-methyl N'-cyano-N- (imidazo[l,2-a]pyridin-7-yl) carbamimidothioate (200mg, 0.865mmol), (4- (phenylsulfonyl)phenyl)methanamine (214mg, 0.865mmol), DMAP (10.56mg, 0.086mmol) and TEA (0.24 lmL, 1.730mmol) in Pyridine (Volume: lOmL) followed by heating the mixture overnight to 70 C. The reaction was monitored by LCMS and then concentrated under reduced pressure and purified directly on the Biotage to give 281mg of product plus starting amine (NMR FT00239-29-A). Material purified again on Biotage again to give the title compound.1H NMR (DMSO-d6): delta 9.39 (br. s, 1H), 8.46 (d, 1H), 7.86-8.00 (m, 6H), 7.56-7.68 (m, 3H), 7.50 (m, 3H), 7.33 (d, 1H), 6.80 (dd, 1H), 4.44 (d, 2H);LC-MS (ESI): 445.15 (M+l).

References: [1]Patent: WO2012/31199,2012,A1 .Location in patent: Page/Page column 82-83.

14
[ 1362754-93-5 ]
[ 94341-56-7 ]
[ 1362752-20-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;dmap; In pyridine;Reflux;	B: 2-cyano-l-(imidazori,2-alpyridin-7-ylmethyl)-3-(4- (phenylsulfonvDbenzyDguanidine:In a 50mL round-bottomed flask was added (Z)-methyl N'-cyano-N- (imidazo[l,2-a]pyridin-7-ylmethyl)carbamimidothioate (400mg, 1.631mmol), (4- (phenylsulfonyl)phenyl)methanamine (403mg, 1.631mmol), DMAP (19.92mg, 0.163mmol) and triethylamine (0.500mL, 3.59mmol) in Pyridine (Volume: lOmL) followed by warming the reaction to 100 C overnight. The reaction was then cooled, diluted with methylene chloride and filtered. The solid was washed with methylene chloride and then dried under vacuum to give 319.5mg of starting cyanoimidate material. LCMS of the mother liquor only showed a trace of product. Took recovered material and added 1 eq. of benzyl amine, 2 eq. of triethylamine and catalytic DMAP in pyridine and refluxed overnight. LCMS showed approx. 50% completion, so continued heating over weekend to force completion. Reaction concentrated under reduced pressure and purified on Biotage to give 262. Omg of product with minor impurity. Triturated material with methylene chloride and filtered to give the title compound.1H NMR (DMSO-d6): delta 8.30 (s, 1H), 7.84-7.93 (m, 5H), 7.74 (t, 1H), 7.54-7.68 (m, 5H), 7.47 (d, 1H), 7.38 (d, 2H), 7.05 (d, 1H), 4.39 (d, 2H), 4.30 (d, 2H);LC-MS (ESI): 445.15 (M+l).

References: [1]Patent: WO2012/31199,2012,A1 .Location in patent: Page/Page column 84.

15
[ 94341-56-7 ]
[ 1362159-51-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 4875 - 4885.

16
[ 94341-56-7 ]
[ 1450723-16-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 4875 - 4885.
[2]Patent: WO2013/127268,2013,A1 .
[3]Journal of Medicinal Chemistry,2016,vol. 59,p. 8345 - 8368.

17
[ 94341-56-7 ]
[ 1362159-82-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 4875 - 4885.

18
[ 94341-56-7 ]
[ 1450723-19-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 4875 - 4885.

19
[ 94341-56-7 ]
[ 1362159-43-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 4875 - 4885.

20
[ 94341-56-7 ]
[ 1362159-41-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 4875 - 4885.

21
[ 94341-56-7 ]
[ 7693-46-1 ]
[ 1450724-06-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	In toluene; at 120℃; for 0.5h;Inert atmosphere;	A mixture of <strong>[94341-56-7][4-(benzenesulfonyl)phenyl]methanamine</strong> (500 mg, 2.02 mmol, 1 .00 equiv) and 4-nitrophenyl chloroformate (500 mg, 2.48 mmol, 1.23 equiv) in toluene (30 mL) was stirred under nitrogen at 120C for 30 min. The reaction mixture was cooled to rt. The solid was collected by filtration, washed with toluene (5 mL) and then dried in vacuum to give 0.8 g (96%) of 4-nitrophenyl N-[[4-(benzenesulfonyl)phenyl]methyl]carbamate as a light yellow solid.

References: [1]Patent: WO2013/127268,2013,A1 .Location in patent: Page/Page column 88.
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 8345 - 8368.
[3]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 4875 - 4885.

22
[ 94341-56-7 ]
[ 710286-63-8 ]
[ 1450723-23-5 ]