55440-54-5|4-Chloro-2-isocyanato-1-methoxybenzene| Ambeed

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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1
[ 55440-54-5 ]
[ 107-19-7 ]
[ 32496-31-4 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide

Reference： [1]Current Patent Assignee: CIBA CO LTD; Novartis (w/o Sandoz); BASF SE; NOVARTIS AG - DE2041986, 1971, A1 [Chem.Abstr., 1971, vol. 75, # 35491][Chem.Abstr., 1971, vol. 75, # 35491]

2
[ 2403-22-7 ]
[ 55440-54-5 ]
[ 88451-17-6 ]

Yield	Reaction Conditions	Operation in experiment
79%	In hexane Ambient temperature;

Reference： [1]DeVries, Vern G.; Bloom, Jonathan D.; Dutia, Minu D.; Katocs, Andrew S.; Largis, Elwood E. [Journal of Medicinal Chemistry, 1989, vol. 32, # 10, p. 2318 - 2325]

3
[ 103-90-2 ]
[ 55440-54-5 ]
4-acetamidophenyl N-(5-chloro-2-methoxyphenyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With triethylamine In acetone for 12h; Heating;

Reference： [1]Vigroux, Alain; Bergon, Michel; Zedde, Chantal [Journal of Medicinal Chemistry, 1995, vol. 38, # 20, p. 3983 - 3994]

4
[ 75-44-5 ]
[ 95-03-4 ]
[ 55440-54-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	In toluene for 4h; Ambient temperature;

Reference： [1]Vigroux, Alain; Bergon, Michel; Zedde, Chantal [Journal of Medicinal Chemistry, 1995, vol. 38, # 20, p. 3983 - 3994]

5
[ 3040-44-6 ]
[ 55440-54-5 ]
2-piperidinoethyl N-(5-chloro-2-methoxyphenyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane for 1.5h; Heating;

Reference： [1]Soulier, Jean-Louis; Yang, Donglai; Brémont, Béatrice; Croci, Tiziano; Guzzi, Umberto; Langlois, Michel [Journal of Medicinal Chemistry, 1997, vol. 40, # 11, p. 1755 - 1761]

6
[ 18717-73-2 ]
[ 55440-54-5 ]
(5-Chloro-2-methoxy-phenyl)-carbamic acid (1R,3R,5S)-8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl ester [ No CAS ]

Reference： [1]Yang; Whirrett; Wu; Wheeler; Childers; Mach [Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S684-S686]

7
[ 55440-54-5 ]
[ 120-29-6 ]
(5-Chloro-2-methoxy-phenyl)-carbamic acid (1R,3R,5S)-8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester [ No CAS ]

Reference： [1]Yang; Whirrett; Wu; Wheeler; Childers; Mach [Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S684-S686]

Yield	Reaction Conditions	Operation in experiment
	5-chloro-2-methoxyaniline, phosgene, ethylacetate;

9
[ 55440-54-5 ]
[ 95-03-4 ]
[ 92550-22-6 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane

Reference： [1]Li; Johnson, Graham; Romine, Jeffrey L; Meanwell, Nicholas A; Martin, Scott W; Dworetzky, Steven I; Boissard, Christopher G; Gribkoff, Valentin K; Starrett Jr., John E [Bioorganic and medicinal chemistry letters, 2003, vol. 13, # 8, p. 1437 - 1439]

10
[ 55440-54-5 ]
[ 76272-58-7 ]
N-(9-benzyl-9-azabicyclo[3.3.1]nonan-3α-yl)-N'-(5-chloro-2-methoxyphenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane at 20℃;

Reference： [1]Mach; Yang; Wu; Kuhner; Whirrett; West [Medicinal Chemistry Research, 2001, vol. 10, # 6, p. 339 - 355]

11
[ 936004-96-5 ]
[ 55440-54-5 ]
1-(5-chloro-2-methoxyphenyl)-3-{6-[2-(dimethylamino)-1-methylethoxy]-pyrazin-2-yl}urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	In toluene Heating;

Reference： [1]Tao, Zhi-Fu; Wang, Le; Stewart, Kent D.; Chen, Zehan; Gu, Wendy; Bui, Mai-Ha; Merta, Philip; Zhang, Haiying; Kovar, Peter; Johnson, Eric; Park, Chang; Judge, Russell; Rosenberg, Saul; Sowin, Thomas; Lin, Nan-Horng [Journal of Medicinal Chemistry, 2007, vol. 50, # 7, p. 1514 - 1527]

12
[ 55440-54-5 ]
[ 78183-55-8 ]
(10aS)-2-(5-chloro-2-methoxyphenyl)-10,10a-dihydroimidazo[1,5-b]isoquinoline-1,3(2H,5H)-dione [ No CAS ]

Reference： [1]Heterocycles,2006,vol. 68,p. 2527 - 2547

14
4-(4-piperidine)-5-methylimidazole, bis hydrochloride salt [ No CAS ]
[ 55440-54-5 ]
[ 335064-79-4 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane at 20℃; for 2h;	169.A Solid 5-chloro-2-methoxyphenylisocyanate (0.77 g, 4.19 mmol) was added to a solution containing 1.0 g (4.19 mmol) of the bis hydrochloride salt of 4-(4-piperidine)-5-methylimidazole (step A Example 127) and 935 mg (9.24 mmol) of triethylamine in 30 mL of CH2Cl2. The solution was stirred for 2 h at RT and concentrated to yield 1.4 g of the crude desired urea as a white solid. The crude material was used without further purification.

Reference： [1]Current Patent Assignee: NEIL STEVEN V O; BRISTOL-MYERS SQUIBB CO - US6887870, 2005, B1 Location in patent: Page/Page column 23; 111

15
[ 791117-28-7 ]
[ 55440-54-5 ]
[ 2252-63-3 ]
{8-fluoro-2-[4-(4-fluorophenyl)-1-piperazinyl]-3-[6-methoxy-3-chlorophenyl]-3,4-dihydro-4-quinazolinyl}-acetic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%

Reference： [1]Current Patent Assignee: AICURIS GMBH & CO. KG - WO2004/96778, 2004, A1 Location in patent: Page/Page column 39

16
[ 1044717-93-2 ]
[ 55440-54-5 ]
1-(5-chloro-2-methoxy-phenyl)-3-{1-[2-(pyrazin-2-ylamino)-pyridin-4-ylmethyl]-1H-indol-4-yl}-urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane for 1h;	1 1-[2-(Pyrazin-2-ylamino)-pyridin-4-ylmethyl]-1H-indol-4-ylamine (45 mg) is dissolved in DCM (5.0 mL) and 4-Chloro-2-isocyanato-1-methoxy-benzene (30 mg) is added and allowed stir for 1 h. Ether (20 mL) is added to the mixture and the precipated solid is collected by vacuum filtration affording 1-(5-chloro-2-methoxy-phenyl)-3-{1-[2-(pyrazin- 2-ylamino)-pyridm-4-ylmethyl]-1H-mdol-4-yl}-urea as a white solid.

Reference： [1]Current Patent Assignee: GILEAD SCIENCES INC - WO2006/76593, 2006, A1 Location in patent: Page/Page column 49-50

17
[ 55440-54-5 ]
[ 613-89-8 ]
N-(5-Chloro-2-methoxyphenyl)-N'-(2-oxo-2-phenylethyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; triethylamine In tetrahydrofuran	39 N-(5-Chloro-2-methoxyphenyl)-N'-(2-oxo-2-phenylethyl)urea (XII39) STR49 EXAMPLE 39 N-(5-Chloro-2-methoxyphenyl)-N'-(2-oxo-2-phenylethyl)urea (XII39) STR49 5-Chloro-2-methoxyphenylisocyanate (5.3 g, 29 mmol) was dissolved in THF (250 ml) under N2 and heated to 60° C. To this solution was added 2-aminoacetophenone. HCl (5 g, 29 mmol) followed by triethylamine (3.8 g, 30 mmol). After being stirred 1.5 h, the reaction mixture was diluted with ethyl acetate (2 vol) and washed with 1N HCl solution, saturated NaCO3 solution, and brine before being dried, MgSO4. Concentration gave a solid which was washed with diethylether 6 g (65%).mp 171°-173° C.; I(KBr, ν=cm-1) 3336, 1706, 1644, 1600, 1560, 1482, 1262, 1220, 1182, 1126; 1 H NMR (300 MHz, CDCl3) δ3.79 (3H, s), 4.84 (2H, d, J=4.3 Hz), 5.97 (1H, br.s), 6.71 (1H, d, J=8.7 Hz), 6.88 (1H, dd, J=8.7 Hz, 2.5 Hz), 7.97-8.00 (2H, m), 8.18 (1H, d, J=2.5 Hz); MS(DCl)m/z: 319(MH+) Anal. calcd. for C16 H15 ClN2 O3: C, 60.29; H, 4.74; N, 8.79. Found: C, 60.17; H, 4.64; N, 8.70.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US5869509, 1999, A

18
[ 190728-25-7 ]
[ 55440-54-5 ]
N-(3-Chloro-6-methoxyphenyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	In toluene	191 N-(3-Chloro-6-methoxyphenyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}urea [227] Example 191 N-(3-Chloro-6-methoxyphenyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}urea [227] 6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (52 mg) was dissolved in toluene (5 ml) with heat, 3-chloro-6-methoxyphenyl isocyanate (111 mg) was added, and the admixture was refluxed with heat for 29 minutes. The resulting residue was purified by column chromatography on silica gel eluding with chloroform/acetone (10/1) to obtain 84 mg of the title compound (yield: 100%). 1 H-NMR (CDCl3, 500 MHz): δ 3.60 (s, 3H), 3.99 (s, 3H), 4.05 (s, 3H), 6.46 (d, J=4.9Hz, 1H), 6.69 (d, J=8.5Hz, 1H), 6.90 (m, 1H), 7.11 (d, J=9.2Hz, 2H), 7.4 2 (s, 1H), 7.5 3 (d, J=8.5Hz, 2H), 7.58 (s, 1H), 7.82 (s, 1H), 8.32 (m, 1H), 8.48 (d, J=5.5Hz, 1H), 8.52 (s, 1H) Mass spectrometry data (FED-MS, m/z): 479 (M+), 481 (M+ +2)

Reference： [1]Current Patent Assignee: KIRIN HOLDINGS CO., LTD. - US6143764, 2000, A

19
[ 2835-78-1 ]
[ 55440-54-5 ]
[ 160384-01-0 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene	10 EXAMPLE 10 EXAMPLE 10 N-(3-benzoylphenyl)-N'-(2-methoxy-5-chlorophenyl) urea. A mixture of 5-chloro-2-methoxyphenyl isocyanate (1.00 g, 5.4 mmol) and 3-aminobenzophenone (1.29 g, 6.5 mmol) was stirred in toluene (20 ml) for two days. The reaction was filtered and the filter cake washed with toluene. 1.9 g of the title compound was isolated.

Reference： [1]Current Patent Assignee: NEUROSEARCH A/S - US5696138, 1997, A

20
[ 915295-41-9 ]
[ 55440-54-5 ]
1-(5-chloro-2-methoxyphenyl)-3-(1-(pyridin-4-ylmethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane at 20℃; for 3h;	1; 2 1-(5-chloro-2-methoxy-phenyl)-3-(1-pyridin-4-ylmethyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-urea (1f) Compound 1d (52 mg, 0.233 mmol) is dissolved in dichloromethane (5.0 mL) and 4-bromo-2-isocyanato-1-methoxy-benzene (1.0 equiv., 44 mg, 0.233 mmol) is then added and stirred at room temperature for 3 hours under nitrogen atmosphere. All solvent is then removed by rotary evaporation and the crude product is purified via preparative TLC to afford Compound 1f as an off-white solid.

Reference： [1]Current Patent Assignee: GILEAD SCIENCES INC - US2006/270702, 2006, A1 Location in patent: Page/Page column 19-20

21
[ 55440-54-5 ]
[ 202823-21-0 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia In tetrahydrofuran at 20℃; for 3h;	30.a a) N-(5-chloro-2-methoxyphenyl)urea; A solution of 4-chloro-2-isocyanato-1-methoxybenzene (18.0 g, 98 mmols) in tetrahydrofuran (60 mL) was added dropwise to a solution of saturated ammonia in the same solvent (240 mL) at room temperature. It was stirred under the same conditions for 3 hours. The pH of the solution obtained was acidic; therefore a stream of ammonia was passed through until a basic pH was reached. The crude was concentrated in vacuo and the solid obtained was triturated with diethylether. It was filtered, washed and dried and it was recristallized from tetrahydrofuran to give the title compound (16.7 g).

Reference： [1]Current Patent Assignee: ALMIRALL SA - WO2006/133802, 2006, A1 Location in patent: Page/Page column 62

22
[ 55440-54-5 ]
[ 170911-92-9 ]
4-{4-[3-(5-chloro-2-methoxy-phenyl)-ureido]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	In tetrahydrofuran at 20℃; for 14.5h;	1 N-tert-butyloxycarbonyl-N'-(4-aminophenyl)-piperazine (138 mg) and 5-chloro-2-methoxyphenyl isocyanate (138 mg) were dissolved in anhydrous tetrahydrofuran (5 mL) and stirred at room temperature for 14.5 hours. After methanol was added to the reaction solution, the mixed solution was concentrated. The obtained solid was vigorously stirred in hexane/isopropyl ether (5:1), collected by filtration and dried under reduced pressure, and 206 mg (89%) of the title compound was obtained as a pale pink crystal. 1H-NMR spectrum (400MHz,DMSO-d6):δ(ppm)=9.15(1H, s), 8.27(1H, s), 8.21(1H, d, J=2.3Hz), 7.29(2H, d, J=9.0Hz), 7.00(1H, d, J=9.0Hz), 6.94(1H, dd, J=8.6 and 2.8Hz), 6.95(2H, d, J=2.8Hz), 3.87(3H, s), 3.44(4H, t, J=4.9Hz), 2.99(4H, t, J=5.1Hz), 1.42(9H, s). MS(FAB) m/z:461 (M + H)+. Melting point: 205°C.

Reference： [1]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - EP1764360, 2007, A1 Location in patent: Page/Page column 98

23
[ 870249-31-3 ]
[ 55440-54-5 ]
[ 919120-19-7 ]
[ 919120-18-6 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane

Reference： [1]Chiu, George; Li, Shengjian; Connolly, Peter J.; Pulito, Virginia; Liu, Jingchun; Middleton, Steven A. [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 2, p. 640 - 644]

24
[ 1029971-74-1 ]
[ 55440-54-5 ]
[ 1029970-20-4 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,8-diazabicyclo[5.4.0]undec-7-ene	48 Example 48 (2Z)-2-(3-butyl-5-methyl-1.3.4-thiadiazol-2(3H)-ylidene)-N-(5-chloro-2- methoxyphenyPacetamideA solution of the product from Example 47A (149 mg, 0.5 mmol), DBU (105 μL, 0.75 mmol) and 5 -chloro -2 -methoxy phenyl isocyanate (91 mg, 0.5 mmol) was stirred overnight. The solution was diluted with water (10 mL), extracted with dichloromethane (3 x 5 mL). The organic layers were combined, washed with brine, dried with sodium sulfate and concentrated in vacuo. The residue was purified by the HPLC procedure specified in Example 47B to obtain the title compound. 1H NMR (300 MHz, DMSO-de) δ ppm 0.93 (t, J= 7.5 Hz, 3 H), 1.27 - 1.39 (m, 2 H), 1.64 - 1.75 (m, 2 H), 2.36 (s, 3 H), 3.82 - 3.91 (m, 5 H), 5.81 (s, 1 H), 6.92 - 7.01 (m, 2 H), 8.36 (d, J= 2.4 Hz, 1 H), 8.68 (s, 1 H); MS (ESI) m/z 354 (M+H)+. Anal. Calcd for Ci6H2oClN302S.0.5 C2HF3O2: C, 48.92; H, 4.92; N, 9.99; Found: C, 49.28; H, 5.09; N, 10.07.

Reference： [1]Current Patent Assignee: ABBVIE INC - WO2008/63781, 2008, A2 Location in patent: Page/Page column 82

25
[ 55440-54-5 ]
[ 60656-84-0 ]
[ 1082940-68-8 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane at 20℃;

Reference： [1]Location in patent: scheme or table Cui, Yong-Mei; Yasutomi, Eriko; Otani, Yuko; Yoshinaga, Takashi; Ido, Katsutoshi; Sawada, Kohei; Ohwada, Tomohiko [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 19, p. 5201 - 5205]

26
[ 879547-76-9 ]
[ 55440-54-5 ]
[ 1160165-44-5 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide at 80 - 90℃; for 4 - 5h;	1 Part II: Preparation of Preferred Compounds of the InventionGeneral method for the preparation of 1-benzyl and 1-propyl indazolone ureas from isocyanates (General method 1)A suspension of 1-benzyl-5-nitro-1,2-dihydro-indazol-3-one (1 eq.) or 1-allyl-5-nitro-1,2-dihydro-indazol-3-one and 10% Pd/C (3-5% equiv.) in MeOH (25 ml per 1 mmol of substrate) was stirred under hydrogen atmosphere (balloon) at room temperature until completion of reduction. After removal of the catalyst and the solvent, the residue was dissolved in acetonitrile (5-15 ml) and the solution was evaporated again. The intermediate reduction product was dried in high vacuum then dissolved in a solvent (DMF or acetonitrile) to make a certain concentration of solution (0.1 to 0.25 based on the solubility). The solution (0.075 mmol) was dispensed to vials followed by adding a desirable isocyanate (0.25 M, 1 equiv.). Then the vials were shaken at 80-90° C. for 4-5 hrs. Solvent removal followed by HPLC purification offered the pure compounds.Example 11-(1-Benzyl-3-oxo-2,3-dihydro-1H-indazol-5-yl)-3-(5-chloro-2-methoxy-phenyl)-urea Following general method 1, described above, 1-(1-benzyl-3-oxo-2,3-dihydro-1H-indazol-5-yl)-3-(5-chloro-2-methoxy-phenyl)-urea was prepared from 1-benzyl-5-nitro-1,2-dihydro-indazol-3-one and 5-chloro-2-methoxyphenyl isocyanate (Yield: 13%). ES-MS calcd for C22H19ClN4O3 (m/e) 422, obsd 423 (M+H). Example 1 1-(1-Benzyl-3-oxo-2,3-dihydro-1H-indazol-5-yl)-3-(5-chloro-2-methoxy-phenyl)-urea Following general method 1, described above, 1-(1-benzyl-3-oxo-2,3-dihydro-1H-indazol-5-yl)-3-(5-chloro-2-methoxy-phenyl)-urea was prepared from 1-benzyl-5-nitro-1,2-dihydro-indazol-3-one and 5-chloro-2-methoxyphenyl isocyanate (Yield: 13%). ES-MS calcd for C22H19ClN4O3 (m/e) 422, obsd 423 (M+H).
	In acetonitrile at 80 - 90℃; for 4 - 5h;	1 Part II: Preparation of Preferred Compounds of the InventionGeneral method for the preparation of 1-benzyl and 1-propyl indazolone ureas from isocyanates (General method 1)A suspension of 1-benzyl-5-nitro-1,2-dihydro-indazol-3-one (1 eq.) or 1-allyl-5-nitro-1,2-dihydro-indazol-3-one and 10% Pd/C (3-5% equiv.) in MeOH (25 ml per 1 mmol of substrate) was stirred under hydrogen atmosphere (balloon) at room temperature until completion of reduction. After removal of the catalyst and the solvent, the residue was dissolved in acetonitrile (5-15 ml) and the solution was evaporated again. The intermediate reduction product was dried in high vacuum then dissolved in a solvent (DMF or acetonitrile) to make a certain concentration of solution (0.1 to 0.25 based on the solubility). The solution (0.075 mmol) was dispensed to vials followed by adding a desirable isocyanate (0.25 M, 1 equiv.). Then the vials were shaken at 80-90° C. for 4-5 hrs. Solvent removal followed by HPLC purification offered the pure compounds.Example 11-(1-Benzyl-3-oxo-2,3-dihydro-1H-indazol-5-yl)-3-(5-chloro-2-methoxy-phenyl)-urea Following general method 1, described above, 1-(1-benzyl-3-oxo-2,3-dihydro-1H-indazol-5-yl)-3-(5-chloro-2-methoxy-phenyl)-urea was prepared from 1-benzyl-5-nitro-1,2-dihydro-indazol-3-one and 5-chloro-2-methoxyphenyl isocyanate (Yield: 13%). ES-MS calcd for C22H19ClN4O3 (m/e) 422, obsd 423 (M+H). Example 1 1-(1-Benzyl-3-oxo-2,3-dihydro-1H-indazol-5-yl)-3-(5-chloro-2-methoxy-phenyl)-urea Following general method 1, described above, 1-(1-benzyl-3-oxo-2,3-dihydro-1H-indazol-5-yl)-3-(5-chloro-2-methoxy-phenyl)-urea was prepared from 1-benzyl-5-nitro-1,2-dihydro-indazol-3-one and 5-chloro-2-methoxyphenyl isocyanate (Yield: 13%). ES-MS calcd for C22H19ClN4O3 (m/e) 422, obsd 423 (M+H).

Reference： [1]Current Patent Assignee: SYNTA PHARMACEUTICALS CORP. - US2009/163546, 2009, A1 Location in patent: Page/Page column 6
[2]Current Patent Assignee: SYNTA PHARMACEUTICALS CORP. - US2009/163546, 2009, A1 Location in patent: Page/Page column 6

27
C₁₃H₁₃N₅ [ No CAS ]
[ 55440-54-5 ]
[ 1349393-47-0 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene at 20℃; for 0.5h;

Reference： [1]Location in patent: experimental part Mitchell, Scott A.; Danca, Mihaela Diana; Blomgren, Peter A.; Darrow, James W.; Currie, Kevin S.; Kropf, Jeffrey E.; Lee, Seung H.; Gallion, Steven L.; Xiong, Jin-Ming; Pippin, Douglas A.; DeSimone, Robert W.; Brittelli, David R.; Eustice, David C.; Bourret, Aaron; Hill-Drzewi, Melissa; Maciejewski, Patricia M.; Elkin, Lisa L. [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 24, p. 6991 - 6995]

28
C₁₂H₁₁N₅ [ No CAS ]
[ 55440-54-5 ]
[ 1348143-62-3 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene at 20℃; for 0.5h;

Reference： [1]Location in patent: experimental part Mitchell, Scott A.; Danca, Mihaela Diana; Blomgren, Peter A.; Darrow, James W.; Currie, Kevin S.; Kropf, Jeffrey E.; Lee, Seung H.; Gallion, Steven L.; Xiong, Jin-Ming; Pippin, Douglas A.; DeSimone, Robert W.; Brittelli, David R.; Eustice, David C.; Bourret, Aaron; Hill-Drzewi, Melissa; Maciejewski, Patricia M.; Elkin, Lisa L. [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 24, p. 6991 - 6995]

29
[ 1044656-17-8 ]
[ 55440-54-5 ]
[ 847024-28-6 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene at 20℃; for 0.5h;

Reference： [1]Location in patent: experimental part Mitchell, Scott A.; Danca, Mihaela Diana; Blomgren, Peter A.; Darrow, James W.; Currie, Kevin S.; Kropf, Jeffrey E.; Lee, Seung H.; Gallion, Steven L.; Xiong, Jin-Ming; Pippin, Douglas A.; DeSimone, Robert W.; Brittelli, David R.; Eustice, David C.; Bourret, Aaron; Hill-Drzewi, Melissa; Maciejewski, Patricia M.; Elkin, Lisa L. [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 24, p. 6991 - 6995]

30
[ 1245210-84-7 ]
[ 55440-54-5 ]
[ 1245211-40-8 ]

Yield	Reaction Conditions	Operation in experiment
28%	In dimethyl sulfoxide at 20℃; for 0.5h;

Reference： [1]Engen, William; O'Brien, Terrence E.; Kelly, Brendan; Do, Jacinda; Rillera, Liezel; Stapleton, Lance K.; Youngren, Jack F.; Anderson, Marc O. [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 16, p. 5995 - 6005]

31
[ 1245210-70-1 ]
[ 55440-54-5 ]
[ 1245211-36-2 ]

Yield	Reaction Conditions	Operation in experiment
41%	In dimethyl sulfoxide at 20℃; for 0.5h;

Reference： [1]Engen, William; O'Brien, Terrence E.; Kelly, Brendan; Do, Jacinda; Rillera, Liezel; Stapleton, Lance K.; Youngren, Jack F.; Anderson, Marc O. [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 16, p. 5995 - 6005]

32
[ 1245210-75-6 ]
[ 55440-54-5 ]
[ 1245211-39-5 ]

Yield	Reaction Conditions	Operation in experiment
4%	In dimethyl sulfoxide at 20℃; for 0.5h;

Reference： [1]Engen, William; O'Brien, Terrence E.; Kelly, Brendan; Do, Jacinda; Rillera, Liezel; Stapleton, Lance K.; Youngren, Jack F.; Anderson, Marc O. [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 16, p. 5995 - 6005]

33
[ 80947-25-7 ]
[ 55440-54-5 ]
[ 1245211-22-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 5995 - 6005

34
[ 55440-54-5 ]
[ 110216-87-0 ]
C₁₇H₁₄ClN₃O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 5995 - 6005

35
[ 55440-54-5 ]
[ 1700-93-2 ]
[ 1245211-04-4 ]

Yield	Reaction Conditions	Operation in experiment
15%	With sodium t-butanolate In dimethyl sulfoxide at 20℃; for 0.5h;

Reference： [1]Engen, William; O'Brien, Terrence E.; Kelly, Brendan; Do, Jacinda; Rillera, Liezel; Stapleton, Lance K.; Youngren, Jack F.; Anderson, Marc O. [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 16, p. 5995 - 6005]

36
[ 504-29-0 ]
[ 55440-54-5 ]
[ 906134-17-6 ]

Yield	Reaction Conditions	Operation in experiment
	In dimethyl sulfoxide at 20℃;

Reference： [1]Location in patent: scheme or table Zhang, Yiqun; Anderson, Marc; Weisman, Jennifer L.; Lu, Min; Choy, Cindy J.; Boyd, Vincent A.; Price, Jeanine; Sigal, Martina; Clark, Julie; Connelly, Michele; Zhu, Fangyi; Guiguemde, W. Armand; Jeffries, Cynthia; Yang, Lei; Lemoff, Andrew; Liou, Ally P.; Webb, Thomas R.; Derisi, Joseph L.; Guy, R. Kiplin [ACS Medicinal Chemistry Letters, 2010, vol. 1, # 9, p. 460 - 465]

37
[ 934-32-7 ]
[ 55440-54-5 ]
[ 912262-93-2 ]

Yield	Reaction Conditions	Operation in experiment
	In dimethyl sulfoxide at 20℃;

Reference： [1]Location in patent: scheme or table Zhang, Yiqun; Anderson, Marc; Weisman, Jennifer L.; Lu, Min; Choy, Cindy J.; Boyd, Vincent A.; Price, Jeanine; Sigal, Martina; Clark, Julie; Connelly, Michele; Zhu, Fangyi; Guiguemde, W. Armand; Jeffries, Cynthia; Yang, Lei; Lemoff, Andrew; Liou, Ally P.; Webb, Thomas R.; Derisi, Joseph L.; Guy, R. Kiplin [ACS Medicinal Chemistry Letters, 2010, vol. 1, # 9, p. 460 - 465]

38
[ 55440-54-5 ]
[ 134-32-7 ]
[ 196868-72-1 ]

Yield	Reaction Conditions	Operation in experiment
	In dimethyl sulfoxide at 20℃;

Reference： [1]Location in patent: scheme or table Zhang, Yiqun; Anderson, Marc; Weisman, Jennifer L.; Lu, Min; Choy, Cindy J.; Boyd, Vincent A.; Price, Jeanine; Sigal, Martina; Clark, Julie; Connelly, Michele; Zhu, Fangyi; Guiguemde, W. Armand; Jeffries, Cynthia; Yang, Lei; Lemoff, Andrew; Liou, Ally P.; Webb, Thomas R.; Derisi, Joseph L.; Guy, R. Kiplin [ACS Medicinal Chemistry Letters, 2010, vol. 1, # 9, p. 460 - 465]

39
[ 55440-54-5 ]
[ 106-47-8 ]
[ 401584-48-3 ]

Yield	Reaction Conditions	Operation in experiment
	In dimethyl sulfoxide at 20℃;

Reference： [1]Location in patent: scheme or table Zhang, Yiqun; Anderson, Marc; Weisman, Jennifer L.; Lu, Min; Choy, Cindy J.; Boyd, Vincent A.; Price, Jeanine; Sigal, Martina; Clark, Julie; Connelly, Michele; Zhu, Fangyi; Guiguemde, W. Armand; Jeffries, Cynthia; Yang, Lei; Lemoff, Andrew; Liou, Ally P.; Webb, Thomas R.; Derisi, Joseph L.; Guy, R. Kiplin [ACS Medicinal Chemistry Letters, 2010, vol. 1, # 9, p. 460 - 465]

40
[ 29568-33-0 ]
[ 55440-54-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium azide / water / 2 h / 20 °C / Inert atmosphere 2: toluene / 1 h / 110 °C
	Multi-step reaction with 2 steps 1: sodium azide / water; acetone / 2 h / 20 °C / Inert atmosphere 2: toluene / 110 °C

Reference： [1]Current Patent Assignee: JIANG - WO2011/23081, 2011, A1
[2]Current Patent Assignee: ASCEPION PHARMACEUTICALS INC - WO2012/28106, 2012, A1

41
[ 55440-54-5 ]
1-(2-methoxy-5-chlorophenyl)-3-[1-(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)-2,3-dihydro-1H-indol-4-yl]urea hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: dichloromethane 2: sodium cyanoborohydride / acetic acid / 1 h / 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 80 °C 4: hydrogenchloride / methanol / 20 °C

Reference： [1]Current Patent Assignee: JIANG - WO2011/23081, 2011, A1

42
[ 55440-54-5 ]
[ 1268390-70-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dichloromethane 2: sodium cyanoborohydride / acetic acid / 1 h / 20 °C
	Multi-step reaction with 2 steps 1: dichloromethane 2: sodium cyanoborohydride / acetic acid / 1 h / 20 °C

Reference： [1]Current Patent Assignee: JIANG - WO2011/23081, 2011, A1
[2]Current Patent Assignee: ASCEPION PHARMACEUTICALS INC - WO2012/28106, 2012, A1

43
[ 55440-54-5 ]
[ 1268390-71-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: dichloromethane 2: sodium cyanoborohydride / acetic acid / 1 h / 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 80 °C

Reference： [1]Current Patent Assignee: JIANG - WO2011/23081, 2011, A1

44
[ 55440-54-5 ]
1-(2-methoxy-5-chlorophenyl)-3-[1-(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)-1H-indol-4-yl]urea hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: dichloromethane 2: sodium cyanoborohydride / acetic acid / 1 h / 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 80 °C 4: 2,3-dicyano-5,6-dichloro-p-benzoquinone / acetone / 20 °C 5: hydrogenchloride / methanol

Reference： [1]Current Patent Assignee: JIANG - WO2011/23081, 2011, A1

45
[ 55440-54-5 ]
[ 1268390-73-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: dichloromethane 2: sodium cyanoborohydride / acetic acid / 1 h / 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 80 °C 4: 2,3-dicyano-5,6-dichloro-p-benzoquinone / acetone / 20 °C

Reference： [1]Current Patent Assignee: JIANG - WO2011/23081, 2011, A1

46
[ 5192-23-4 ]
[ 55440-54-5 ]
[ 1268390-69-7 ]

Yield	Reaction Conditions	Operation in experiment
70%	In dichloromethane	1 A solution of 5-chloro-2-methoxyphenyl isocyanate (Int-4, 5.5 g, 30 mmol) in DCM (20 mL) was added dropwise to the 4-amino- lH-indole in DCM (30 mL) from Step A, and the resulting mixture was stirred overnight, then filtered to give the crude product l-(5-chloro-2-methoxyphenyl)-3-(lH-indol-4-yl)urea (6.6 g, 70%), which was used directly in the next step without purification.

Reference： [1]Current Patent Assignee: JIANG - WO2011/23081, 2011, A1 Location in patent: Page/Page column 56

47
[ 1268390-76-6 ]
[ 55440-54-5 ]
1-(2-methoxy-5-chlorophenyl)-3-[1-(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)-1H-indol-4-yl]urea hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dichloromethane 2: hydrogenchloride / methanol

Reference： [1]Current Patent Assignee: JIANG - WO2011/23081, 2011, A1

48
[ 1268390-76-6 ]
[ 55440-54-5 ]
[ 1268390-73-3 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane	2b To a solution of 4-[(4-amino- lH-indol- 1 -yl)methyl]- 1 -(/-butyloxycarbonyl)- lH-pyrrolo[2,3-6]pyridine (450 mg) in DCM was added 5-chloro-2-methoxyphenyl isocyanate (Int-4, 275 mg, 1.5 mmol). The mixture was stirred overnight, then concentrated, and purified by flash column chromatography to give the desired product 1 -(2-methoxyl-5-chlorophenyl)-3-{l-[l-(?-butyloxycarbonyl)-lH-pyrrolo[2,3-]pyridin-4- ylmethyl]-lH-indol-4-yl}urea (540 mg, 80% for two steps).1H NMR (400 MHz, CDCl3): δ 8.40 (d, J = 1.6, IH), 8.34 (s, J = 4.2, IH), 7.91 (s, IH),7.76 (s, IH), 7.63 (d, J = 4.0, IH), 7.46 (d, J = 7.6, IH), 7.12 (t, J = 8.0, IH), 7.03 (d, J= 3.2, IH), 6.96 (J = 8.4, IH), 6.90, 6.87 (dd, J = 8.8, 2.8, IH), 6.68-6.64 (m, 3H), 6.27(d, J = 4.4, IH), 5.51 (s, 2H), 3.60 (s, 3H), 1.66 (s, 9H).

Reference： [1]Current Patent Assignee: JIANG - WO2011/23081, 2011, A1 Location in patent: Page/Page column 59

49
[ 1268390-80-2 ]
[ 55440-54-5 ]
[ 1268390-81-3 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene	3 A solution of 3-[(4-amino- lH-indol- 1 -yl)methyl]- 1 -(^-butyloxycarbonyl)- IH- pyrrolo[2,3-6]pyridine from previous step and 5-chloro-2-methoxyphenyl isocyanate(Int-14, 275 mg, 1.5 mmol) in toluene was stirred overnight. The reaction mixture was concentrated and purified by flash column chromatography to afford product l-(2- methoxyl-5-chlorophenyl)-3- { 1 -[ 1 -(^-butyloxycarbonyl)- lH-pyrrolo[2,3-6]pyridin-3- ylmethyl]-lH-indol-4-yl}urea (518 mg, 73% for two steps).1H NMR (400 MHz, CDCl3): δ 8.49 (d, J = 5.2, IH), 8.33 (s, IH), 7.65 (s, IH), 7.56 (s,IH), 7.50 (d, J = 8.0, IH), 7.31 (t, J = 6.8, 2H), 7.26-7.25 (m, IH), 7.14 (s, IH), 7.09 (t, J= 6.0, IH), 6.91 (d, J = 8.8, IH), 6.71-6.68 (m, 2H), 6.57 (s, IH), 5.41 (s, 2H), 3.64 (s,3H), 1.67 (s, 9H).

Reference： [1]Current Patent Assignee: JIANG - WO2011/23081, 2011, A1 Location in patent: Page/Page column 60

50
[ 3438-16-2 ]
[ 55440-54-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: thionyl chloride / dichloromethane / 2 h / Inert atmosphere; Reflux 2: sodium azide / water / 2 h / 20 °C / Inert atmosphere 3: toluene / 1 h / 110 °C
	Multi-step reaction with 3 steps 1: thionyl chloride / dichloromethane / 2 h / Inert atmosphere; Reflux 2: sodium azide / water; acetone / 2 h / 20 °C / Inert atmosphere 3: toluene / 110 °C

Reference： [1]Current Patent Assignee: JIANG - WO2011/23081, 2011, A1
[2]Current Patent Assignee: ASCEPION PHARMACEUTICALS INC - WO2012/28106, 2012, A1

51
[ 1152958-89-8 ]
[ 55440-54-5 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene at 110℃; for 1h;	I The acyl azide Int-3 obtained from previous step was dissolved in dry toluene(100 mL). The resulted solution was added slowly to an empty round-bottom flask preheated in an oil bath at 110 0C. Evolution of nitrogen was observed, which ceased after about 1 h of addition. The reaction mixture was then cooled to room temperature and solvent was removed under reduced pressure to yield a yellowish solid residue, which was recrystallized from petroleum ether to afford the desired product Int-4 as white crystals (10.3 g, 56% for 3 steps), which turn yellowish on standing.MS (ESI+): m/z 238.0 (100) [M+MeOH+Na, 35Cl]+, 240.0 (33) [M+MeOH+Na, 37Cl]+.
	In toluene at 110℃;	I [123] The acyl azide Int-3 obtained from previous step was dissolved in dry toluene (100 mL). The resulted solution was added slowly to an empty round-bottom flask preheated in an oil bath at 110 °C. Evolution of nitrogen was observed, which ceased after about 1 h of addition. The reaction mixture was then cooled to room temperature and solvent was removed under reduced pressure to yield a yellowish solid residue, which was recrystallized from petroleum ether to afford the desired product Int-4 as white crystals (10.3 g, 56% for 3 steps), which turn yellowish on standing.MS (ESI+): m/z 238.0 [M+MeOH+Na, 35C1]+, 240.0 [M+MeOH+Na, 37C1]+.

Reference： [1]Current Patent Assignee: JIANG - WO2011/23081, 2011, A1 Location in patent: Page/Page column 51
[2]Current Patent Assignee: ASCEPION PHARMACEUTICALS INC - WO2012/28106, 2012, A1 Location in patent: Page/Page column 44-45

52
[ 10569-72-9 ]
[ 55440-54-5 ]
[ 1337961-54-2 ]

Yield	Reaction Conditions	Operation in experiment
57%	In methanol at 20℃;

Reference： [1]Location in patent: experimental part De Filippis, Barbara; Giampietro, Letizia; Giancristofaro, Antonella; Ammazzalorso, Alessandra; Fantacuzzi, Marialuigia; Maccallini, Cristina; Petruzzelli, Michele; Amoroso, Rosa [Letters in drug design and discovery, 2011, vol. 8, # 2, p. 154 - 158]

53
[ 55440-54-5 ]
[ 1362855-49-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: dichloromethane 2: sodium cyanoborohydride / acetic acid / 1 h / 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 80 °C

Reference： [1]Current Patent Assignee: ASCEPION PHARMACEUTICALS INC - WO2012/28106, 2012, A1

54
[ 55440-54-5 ]
[ 1362855-50-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: dichloromethane 2: sodium cyanoborohydride / acetic acid / 1 h / 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 80 °C 4: 2,3-dicyano-5,6-dichloro-p-benzoquinone / acetone / 20 °C

Reference： [1]Current Patent Assignee: ASCEPION PHARMACEUTICALS INC - WO2012/28106, 2012, A1

55
[ 55440-54-5 ]
[ 1362852-56-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: dichloromethane 2: sodium cyanoborohydride / acetic acid / 1 h / 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 80 °C 4: 2,3-dicyano-5,6-dichloro-p-benzoquinone / acetone / 20 °C 5: hydrogenchloride / methanol / 60 °C

Reference： [1]Current Patent Assignee: ASCEPION PHARMACEUTICALS INC - WO2012/28106, 2012, A1

56
[ 55440-54-5 ]
[ 1362852-54-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: dichloromethane 2.1: sodium cyanoborohydride / acetic acid / 1 h / 20 °C 3.1: potassium carbonate / N,N-dimethyl-formamide / 80 °C 4.1: trifluoroacetic acid / 1 h / 20 °C 4.2: 0.5 h / pH 7 - 8

Reference： [1]Current Patent Assignee: ASCEPION PHARMACEUTICALS INC - WO2012/28106, 2012, A1

57
[ 5192-23-4 ]
[ 55440-54-5 ]
1-(5-chloro-2-methoxyphenyl)-3-(1H-indol-4-yl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane	VII A solution of 5-chloro-2-methoxyphenyl isocyanate (Int-4, 5.5 g, 30 mmol) in DCM (20 mL) was added dropwise to the 4-amino-lH-indole in DCM (30 mL), and the resulting mixture was stirred overnight, then filtered to give the crude product l-(5-chloro-2- methoxyphenyl)-3-(lH-indol-4-yl)urea (lnt-29, 6.6 g, 70%>), which was used directly in the next step without purification.

Reference： [1]Current Patent Assignee: ASCEPION PHARMACEUTICALS INC - WO2012/28106, 2012, A1 Location in patent: Page/Page column 50

58
[ 55440-54-5 ]
9-benzyl-1-oxa-9-azaspiro[5.5]undecan-4-amine [ No CAS ]
N-(9-benzyl-1-oxa-9-azaspiro[5.5]undec-4-yl)-N′-(5-chloro-2-methoxyphenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48.1%	In diethyl ether at 20℃; Inert atmosphere;	4.2.6. General procedure for preparation of compounds 33-45 General procedure: 9-Benzyl-1-oxa-9-azaspiro[5.5]undecan-4-amine (7, 156 mg, 0.60 mmol) was dissolved in diethyl ether (8 mL) and treated with the respective isocyanate (0.63 mL, added dropwise). The resulting mixture was stirred overnight. The precipitate formed was separated by filtration, washed with diethyl ether and dried in vacuo to provide the title compound.

Reference： [1]Lukin, Alexey; Kramer, Jan; Hartmann, Markus; Weizel, Lilia; Hernandez-Olmos, Victor; Falahati, Konstantin; Burghardt, Irene; Kalinchenkova, Natalia; Bagnyukova, Darya; Zhurilo, Nikolay; Rautio, Jarkko; Forsberg, Markus; Ihalainen, Jouni; Auriola, Seppo; Leppänen, Jukka; Konstantinov, Igor; Pogoryelov, Denys; Proschak, Ewgenij; Dar'in, Dmitry; Krasavin, Mikhail [Bioorganic Chemistry, 2018, vol. 80, p. 655 - 667]

59
[ 55440-54-5 ]
2-(4-chloro-2-ureidophenoxy)-N-((3-endo)-8-(4-chlorobenzyl)-8-azabicyclo[3.2.1]octan-3-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: ammonia / tetrahydrofuran / 3 h / 20 °C 2.1: boron tribromide / dichloromethane / -10 - 20 °C 2.2: 0 °C 3.1: potassium carbonate / N,N-dimethyl-formamide / 20 - 50 °C

Reference： [1]Current Patent Assignee: ALMIRALL SA - WO2006/133802, 2006, A1

60
[ 55440-54-5 ]
2-(4-chloro-2-ureidophenoxy)-N-((3-endo)-8-(4-fluorobenzyl)-8-azabicyclo[3.2.1]octan-3-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: ammonia / tetrahydrofuran / 3 h / 20 °C 2.1: boron tribromide / dichloromethane / -10 - 20 °C 2.2: 0 °C 3.1: potassium carbonate / N,N-dimethyl-formamide / 20 - 50 °C

Reference： [1]Current Patent Assignee: ALMIRALL SA - WO2006/133802, 2006, A1

61
[ 55440-54-5 ]
[ 57718-28-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: ammonia / tetrahydrofuran / 3 h / 20 °C 2.1: boron tribromide / dichloromethane / -10 - 20 °C 2.2: 0 °C

Reference： [1]Current Patent Assignee: ALMIRALL SA - WO2006/133802, 2006, A1

62
[ 55440-54-5 ]
N-[2-(4-aminophenyl)ethyl]-7-ethoxy-6-fluoroquinazolin-4-amine [ No CAS ]
1-(5-chloro-2-methoxyphenyl)-3-(4-{2-[(7-ethoxy-6-fluoroquinazolin-4-yl)amino]ethyl}phenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In methanol; dichloromethane at 20℃; for 2h; Inert atmosphere;	General Procedure B General procedure: To a solution of amine derivatives 19a-f (1.0 equiv.) in dichloromethane (0.5-30mL) or N,N-dimethylformamide (1mL) and was added appropriate isocyanate (1.0-2.1 equiv.) and methanol (0-0.20mL) then the reaction mixture was stirred at room temperature. After stirred for 1-16h, the resulting precipitate was collected, washed with dichloromethane (5-20mL) and dried in vacuo to yield the title compounds 20-23, 25-39 in 28-98% yield.

Reference： [1]Chang, Ling; Chen, Ching-Ping; Chen, Chiung-Tong; Chen, Pei-Yi; Chiu, Chun-Hsien; Fan, Chu-Min; Hsieh, Hsing-Pang; Huang, Chen-Lung; Li, Mu-Chun; Lin, Wen-Hsing; Su, Yu-Chieh; Wang, Pei-Chen; Yeh, Teng-Kuang [European Journal of Medicinal Chemistry, 2021, vol. 224]

63
[ 55440-54-5 ]
[ 78553-63-6 ]
N<SUP>1</SUP>-(5-chloro-2-methoxyphenyl)-N<SUP>3</SUP>-octylmalonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	Stage #1: N-Octyl-3-oxo-butyramide With potassium hydroxide; magnesium(II) chloride In dichloromethane at 25℃; for 0.5h; Inert atmosphere; Stage #2: 2-methoxy-5-chlorophenyl isocyanate In dichloromethane at 25℃; for 1h; Inert atmosphere;

Reference： [1]Cao, Xiyang; Wang, Gang; Zhang, Guisheng; Zhang, Xingjie; Zhang, Zhiguo [Green Chemistry, 2022, vol. 24, # 7, p. 3035 - 3041]

CAS No. :	55440-54-5	MDL No. :	MFCD00013860
Formula :	C₈H₆ClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CDRZZFCLBUGMMB-UHFFFAOYSA-N
M.W :	183.59	Pubchem ID :	144009
Synonyms :

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P280-P305+P351+P338-P342+P311	UN#:	2811
Hazard Statements:	H302-H312-H315-H319-H332-H334-H335	Packing Group:	Ⅲ
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
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.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
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.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
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. 55440-54-5 ] {[proInfo.proName]}

Quality Control of [ 55440-54-5 ]

Related Doc. of [ 55440-54-5 ]

Product Details of [ 55440-54-5 ]

Safety of [ 55440-54-5 ]

Application In Synthesis of [ 55440-54-5 ]

[ 55440-54-5 ] Synthesis Path-Downstream 1~63

Related Functional Groups of
[ 55440-54-5 ]

Aryls

Chlorides

Ethers

Isocyanates and Isothiocyanates

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

[ CAS No. 55440-54-5 ] {[proInfo.proName]}

Quality Control of [ 55440-54-5 ]

Related Doc. of [ 55440-54-5 ]

Product Details of [ 55440-54-5 ]

Safety of [ 55440-54-5 ]

Application In Synthesis of [ 55440-54-5 ]

[ 55440-54-5 ] Synthesis Path-Downstream 1~63

Related Functional Groups of [ 55440-54-5 ]

Aryls

Chlorides

Ethers

Isocyanates and Isothiocyanates

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 55440-54-5 ]