[ CAS No. 59669-59-9 ]

Name: 59669-59-9|3-(tert-Butyl)isoxazol-5-amine|95%
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Quality Control of [ 59669-59-9 ]

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Product Details of [ 59669-59-9 ]

CAS No. :	59669-59-9	MDL No. :	MFCD05266697
Formula :	C₇H₁₂N₂O	Boiling Point :	248.1°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	140.18 g/mol	Pubchem ID :	2095694
Synonyms :

Calculated chemistry of of [ 59669-59-9 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.57
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	40.18
TPSA :	52.05 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.93 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.74
Log Po/w (XLOGP3) :	1.73
Log Po/w (WLOGP) :	1.56
Log Po/w (MLOGP) :	0.87
Log Po/w (SILICOS-IT) :	1.12
Consensus Log Po/w :	1.41

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.1
Solubility :	1.11 mg/ml ; 0.00789 mol/l
Class :	Soluble
Log S (Ali) :	-2.44
Solubility :	0.51 mg/ml ; 0.00364 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.06
Solubility :	1.21 mg/ml ; 0.00865 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.55

Safety of [ 59669-59-9 ]

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:

Application In Synthesis of [ 59669-59-9 ]

* 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.

Upstream synthesis route of [ 59669-59-9 ]
Downstream synthetic route of [ 59669-59-9 ]

[ 59669-59-9 ] Synthesis Path-Upstream 1~6

1
[ 59997-51-2 ]
[ 59669-59-9 ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium hydroxide; hydroxylamine hydrochloride In water at 50℃; for 3 h;	To an aqueous solution of sodium hydroxide solution (40.00 g, 1 mol, in 200 ml of water) was added hydroxylamine hydrochloride (24.00 g, 346 mmol) and pivaloylacetonitrile (40.00 g, 320 mmol). The resulting solution was stirred at 50° C. for 3 hrs. The reaction mixture cooled and the resultant white crystalline solid filtered, washed with water and dried to provide 3-t-butylisoxazol-5-amine as a white crystalline solid (34 g, yield 76percent yield). ¹H NMR (DMSO-d₆) δ 6.41 (brs, 2H), 4.85 (s, 1H), 1.18(s, 9H): LC-MS (ES, m/z, M+H) 141.3.

Reference： [1] Heterocycles, 1991, vol. 32, # 6, p. 1153 - 1158
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 3, p. 1082 - 1105
[3] Patent: US2008/261961, 2008, A1, . Location in patent: Page/Page column 16
[4] Organic Letters, 2018, vol. 20, # 9, p. 2774 - 2777
[5] Journal of Medicinal Chemistry, 2016, vol. 59, # 18, p. 8293 - 8305
[6] Chemische Berichte, 1932, vol. 65, p. 1857,1862
[7] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 18, p. 2047 - 2050
[8] Patent: WO2010/77836, 2010, A2, . Location in patent: Page/Page column 131
[9] Molecules, 2014, vol. 19, # 2, p. 2004 - 2028
[10] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 17, p. 3436 - 3441

2
[ 59997-51-2 ]
[ 59669-59-9 ]
[ 121449-41-0 ]

Reference： [1] Dyes and Pigments, 2010, vol. 86, # 1, p. 42 - 49

3
[ 3938-95-2 ]
[ 59669-59-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 17, p. 3436 - 3441
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 18, p. 8293 - 8305

4
[ 59669-54-4 ]
[ 59669-59-9 ]

Reference： [1] Chemical & Pharmaceutical Bulletin, 1984, vol. 32, # 7, p. 2736 - 2744
[2] Chemical & Pharmaceutical Bulletin, 1984, vol. 32, # 7, p. 2736 - 2744

5
[ 59669-59-9 ]
[ 15673-05-9 ]
[ 55809-36-4 ]

Yield	Reaction Conditions	Operation in experiment
52%	With lithium hydroxide; hydroxylamine hydrochloride In ethanol; water	EXAMPLE 2 Preparation of 3-amino-5-(t-butyl)isoxazole In a 1 l. 3-neck round bottom flask there was placed 30 g. of pivalyl acetonitrile, 13.5 g. of lithium hydroxide, 394 ml. of water and 281 ml. of ethanol. This mixture was heated to reflux and there was added thereto over a period of 10 minutes 94 ml. of an aqueous solution of 22.2 g. of hydroxylamine hydrochloride. The pH of the reaction mixture after the addition was complete was about 7.3. This pH was adjusted to about pH 6.7 using concentrated aqueous hydrochloric acid. After 30 minutes the pH was about 6.1. After 1 hour the pH was about 6.3. The pH was checked again at 2 hours and at 3 hours after the addition was complete and the pH at those times was about 6.6. A recheck of the pH at 4 hours, 5 hours, and 6 hours revealed the pH to be at about 6.7. The reaction mixture was then refluxed overnight. The following morning the pH was about 6.8. The reaction mixture was cooled and the ethanol removed from the mixture on the rotovapor at room temperature. A solid which separated was filtered off and dried. It weighed 18.65 g. and it was determined by vpc that the product contained 97percent of the desired 3-amino-5-(t-butyl)isoxazole, and 1.6percent of 5-amino-3-(t-butyl)isoxazole. Yield: 52percent of desired isomer.

Reference： [1] Patent: US4259501, 1981, A,

6
[ 59669-59-9 ]
[ 121449-41-0 ]
[ 55809-36-4 ]
[ 136320-07-5 ]
[ 75914-61-3 ]

Reference： [1] Heterocycles, 1991, vol. 32, # 6, p. 1153 - 1158

[ 59669-59-9 ] Synthesis Path-Downstream 1~31

1
[ 59997-51-2 ]
[ 59669-59-9 ]

Yield	Reaction Conditions	Operation in experiment
88%	With hydroxylamine hydrochloride; sodium hydroxide; In water; at 60℃; for 3h;	A solution of sodium hydroxide (250g. 6.25 mol) in water (1250 ml) was added with pivaloylacetonitrile (CAS: 59997-51-2, 250g, 2.0 mol) followed by hydroxylaminehydrochloride (150g, 2.16 mol). The mixture was heated to 60 C during which time it became homogeneous and then began to deposit a solid. After 3h the mixture was cooled to RT and the solid removed by filtration, washed well with water and dried at 45C under vacuum to give the title compound (245.1g. 88%). The aqueous filtrate was extracted with DCM (2 x 100 ml) and the combined DCM layers were dried (Na2SO4) and evaporated.(10.9g,4%).?H NMR (300MHz, CDC13) 1.28 (9H, s), 4.31 (2H, br s), 5.03 (111, s).
76%	With sodium hydroxide; hydroxylamine hydrochloride; In water; at 50℃; for 3h;	To an aqueous solution of sodium hydroxide solution (40.00 g, 1 mol, in 200 ml of water) was added hydroxylamine hydrochloride (24.00 g, 346 mmol) and pivaloylacetonitrile (40.00 g, 320 mmol). The resulting solution was stirred at 50 C. for 3 hrs. The reaction mixture cooled and the resultant white crystalline solid filtered, washed with water and dried to provide 3-t-butylisoxazol-5-amine as a white crystalline solid (34 g, yield 76% yield). 1H NMR (DMSO-d6) delta 6.41 (brs, 2H), 4.85 (s, 1H), 1.18(s, 9H): LC-MS (ES, m/z, M+H) 141.3.
	With hydroxyammonium sulfate; sodium hydroxide; In water; for 2h;Reflux;	Step 1: Synthesis of 3-tert-butyl-isoxazol-5-ylamine; Hydroxylamine sulfate (27.575g, 0.168mol) is added to a stirred solution of 4,4-dimethyl-3- oxopentanenitrile (2Og; O.lOmol) and sodium hydroxide (26.24g; 0.656mol) in water (16OmL). The mixture is heated at reflux for 2 hours, then allowed to cool to room temperature and extracted with methylene chloride. The combined organics are washed with water, dried (Na2SO4), filtered and concentrated in vacuo to afford title compound as a white solid. ESI m/z 141 [M+H]+

With hydroxylamine hydrochloride; sodium hydroxide; In water; at 50℃; for 3h;

To an aqueous solution of sodium hydroxide solution (0.84 g,21 mmol) in water (10 mL), pivaloylacetonitrile (1.25 g, 10 mmol) and hydroxylamine hydrochloride(0.76 g, 11 mmol) were added. The resulting solution was stirred at 50 C for 3 h. The reaction mixture was cooled and the resultant white crystalline solid was filtered, washed with water and dried to provide compound 25r as a white crystalline solid (1.23 g, yield 88%).

Reference： [1]Heterocycles,1991,vol. 32,p. 1153 - 1158
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 1082 - 1105
[3]Patent: WO2018/224423,2018,A1 .Location in patent: Page/Page column 64
[4]Patent: US2008/261961,2008,A1 .Location in patent: Page/Page column 16
[5]Organic Letters,2018,vol. 20,p. 2774 - 2777
[6]Journal of Organic Chemistry,2019,vol. 84,p. 2676 - 2688
[7]Journal of Medicinal Chemistry,2016,vol. 59,p. 8293 - 8305
[8]Chemische Berichte,1932,vol. 65,p. 1857,1862
[9]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 2047 - 2050
[10]Patent: WO2010/77836,2010,A2 .Location in patent: Page/Page column 131
[11]Molecules,2014,vol. 19,p. 2004 - 2028
[12]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3436 - 3441

2
[ 59669-59-9 ]
[ 20432-35-3 ]
[ 93241-51-1 ]

Reference： [1]Chemical and pharmaceutical bulletin,1984,vol. 32,p. 2736 - 2744

3
[ 59669-59-9 ]
[ 121449-41-0 ]
[ 55809-36-4 ]
[ 136320-07-5 ]
[ 75914-61-3 ]

Reference： [1]Heterocycles,1991,vol. 32,p. 1153 - 1158

4
[ 59669-59-9 ]
[ 75914-61-3 ]

Reference： [1]Heterocycles,1991,vol. 32,p. 1153 - 1158

5
[ 59669-54-4 ]
[ 59669-59-9 ]

Reference： [1]Chemical and pharmaceutical bulletin,1984,vol. 32,p. 2736 - 2744
[2]Chemical and pharmaceutical bulletin,1984,vol. 32,p. 2736 - 2744

6
[ 59669-59-9 ]
[ 327-78-6 ]
N-(3-tert-butyl-5-isoxazolyl)-N'-(4-chloro-3-(trifluoromethyl)phenyl)urea [ No CAS ]
bis(4-chloro-3-(trifluoromethyl)phenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With Dowex.(R). 50WX2-100 resin; In toluene; at 85℃; for 24h;	To a solution of <strong>[59669-59-9]5-amino-3-tert-butylisoxazole</strong> (0.100 g) in anh toluene (5 mL) was added 4-chloro-3-(trifluoromethyl)phenyl isocyanate (0.395 g). The reaction vessel was sealed, heated at 85 °C for 24 h, and cooled to room temp. The reaction mixture was added to a slurry of Dowex.(R). 50WX2-100 resin (0.5 g) in CH2Cl2 (40 mL), and the resulting mixture was stirred vigorously for 72 h. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (gradient form 100percent CH2Cl2 to 5percent MeOH/95percent CH2Cl2) to give bis(4-chloro-3-(trifluoromethyl)phenyl)urea followed by N-(3-tert-butyl-5-isoxazolyl)-N'-(4-chloro-3-(trifluoromethyl)phenyl)urea. The residue from the symmetrical urea fractions was triturated (Et2O/hexane) to give the urea as a white solid (0.110 g): TLC (3percent MeOH/97percent CH2Cl2) Rf 0.55; FAB-MS m/z 417 ((M+H)+).
		B6. General Method for the Synthesis of Symmetrical Diphenyl Ureas as Side-Products of Urea Forming reactions ; [] Bis(4-chloro-3-(trifluoromethyl)phenyl)urea: To a solution of <strong>[59669-59-9]5-amino-3-tert-butylisoxazole</strong> (0.100 g) in anh toluene (5 mL) was added 4-chloro-3-(trifluoromethyl)phenyl isocyanate (0.395 g). The reaction vessel was sealed, heated at 85 °C for 24 h, and cooled to room temp. The reaction mixture was added to a slurry of Dowex.(R). 50WX2-100 resin (0.5 g) in CH2Cl2 (40 mL), and the resulting mixture was stirred vigorously for 72 h. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (gradient form 100percent CH2Cl2 to 5percent MeOH/95percent CH2Cl2) to give bis(4-chloro-3-(trifluoromethyl)phenyl)urea followed by N-(3-tert-butyl-5-isoxazolyl)-N'-(4-chloro-3-(trifluoromethyl)phenyl)urea. The residue from the symmetrical urea fractions was triturated (Et2O/hexane) to give the urea as a white solid (0.110 g): TLC (3percent MeOH/97percent CH2Cl2) Rf 0.55; FAB-MS m/z 417 ((M+H)+).

Reference： [1]Patent: EP1449834,2004,A2 .Location in patent: Page 39
[2]Patent: EP1042305,2005,B1 .Location in patent: Page/Page column 44

7
[ 75-44-5 ]
[ 59669-59-9 ]
[ 59669-71-5 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In dichloromethane; toluene; at 20℃; for 1h;	C2a. Reaction of a Heterocyclic Amine with Phosgene to Form an Isocyanate, then Reaction with Substituted Aniline; Step 1. 3-tert-Butyl-5-isoxazolyl Isocyanate; To a solution of phosgene (20percent in toluene, 1.13 mL, 2.18 mmol) in CH2Cl2 (20 mL) at 0° C. was added anh. pyridine (0.176 mL, 2.18 mmol), followed by <strong>[59669-59-9]5-amino-3-tert-butylisoxazole</strong> (0.305 g, 2.18 mmol). The resulting solution was allowed to warm to room temp. over 1 h, and then was concentrated under reduced pressure. The solid residue dried in vacuo for 0.5 h.
	With pyridine; In dichloromethane; toluene; at 0 - 20℃;	Step 1.3-tert-Butyl-5-isoxazolyl Isocyanate To a solution of phosgene (20percent in toluene, 1.13 mL, 2.18 mmol) in CH2Cl2 (20 mL) at 0° C. was added anh. pyridine (0.176 mL, 2.18 mmol), followed by <strong>[59669-59-9]5-amino-3-tert-butylisoxazole</strong> (0.305 g, 2.18 mmol).The resulting solution was allowed to warm to room temp. over 1 h, and then was concentrated under reduced pressure.The solid residue dried in vacuo for 0.5 h.
	With pyridine; In dichloromethane; toluene; at 20℃; for 1h;	To a solution of phosgene (20percent in toluene, 1.13 mL, 2.18 mmol) in CH2Cl2 (20 mL) at 0 °C was added anh. pyridine (0.176 mL, 2.18 mmol), followed by <strong>[59669-59-9]5-amino-3-tert-butylisoxazole</strong> (0.305 g, 2.18 mmol). The resulting solution was allowed to warm to room temp. over 1 h, and then was concentrated under reduced pressure. The solid residue dried in vacuo for 0.5 h.

Reference： [1]Patent: US2007/244120,2007,A1 .Location in patent: Page/Page column 25
[2]Patent: US2012/46290,2012,A1 .Location in patent: Page/Page column 25
[3]Patent: EP1047418,2005,B1 .Location in patent: Page/Page column 41

8
[ 59669-59-9 ]
[ 79-04-9 ]
[ 668980-81-2 ]

Yield	Reaction Conditions	Operation in experiment
97%	With pyridine; In dichloromethane; at 0 - 20℃; for 2h;	[CHLOROACETIC] acid chloride (0.25 ml ; 3.14 [MMOL)] is dropped slowly into a stirred solution of 3-t-Butyl-5-amino isoxazole (400 mg; 2.85 [MMOL)] in pyridine (0.3 ml ; 3.71 [MMOL)] and dichloromethane (2 [ ML),] cooled to 0 C. Stirring is continued for 2 h at room temperature. The reaction mixture is diluted with [DICHLOROMETHANE,] washed twice with 1 N aqueous hydrochloric acid, twice with an aqueous solution of [NAHCO3] and with water. The reaction mixture is then dried over [NA2SO4,] filtered and evaporated to yield 600 mg (97 [%)] brownish solid of 11.

Reference： [1]Patent: WO2004/19941,2004,A1 .Location in patent: Page/Page column 159; 160

9
[ 59669-59-9 ]
[ 59377-19-4 ]
N-(3-tert-butyl-5-isoxazolyl)-N'-(4-phenoxyphenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	In dichloromethane; for 48h;Heating / reflux;	C1b. Reaction of a Heterocyclic Amine with an Isocyanate; N-(3-tert-Butyl-5-isoxazolyl)-N'-(4-phenoxyphenyl)urea; To a solution of <strong>[59669-59-9]5-amino-3-tert-butylisoxazole</strong> (8.93 g, 63.7 mmol, 1 eq.) in CH2Cl2 (60 mL) was added 4-phenyloxyphenyl isocyanate (15.47 g, 73.3 mmol, 1.15 eq.) dropwise. The mixture was heated at the reflux temp. for 2 days, eventually adding additional CH2Cl2 (80 mL). The resulting mixture was poured into water (500 mL) and extracted with Et2O (3.x.200 mL). The organic layer was dried (MgSO4) then concentrated under reduced pressure. The residue was recrystallized (EtOAc) to give the desired product (15.7 g, 70percent): mp 182-184° C.; TLC (5percent acetone/95percent acetone) Rf 0.27; 1H-NMR (DMSO-d6) delta 1.23 (s, 9H), 6.02 (s, 1H), 6.97 (dd, J=0.2, 8.8 Hz, 2H), 6.93 (d, J=8.8 Hz, 2H), 7.08 (t, J=7.4 Hz, 1H), 7.34 (m, 2H), 7.45 (dd, J=2.2, 6.6 Hz, 2H), 8.80 (s, 1H), 10.04 (s, 1H); FAB-MS m/z (rel abundance) 352 ((M+H)+, 70percent).
70%	In dichloromethane; for 48h;Reflux;	N-(3-tert-Butyl-5-isoxazolyl)-N'-(4-phenoxyphenyl)urea: To a solution of <strong>[59669-59-9]5-amino-3-tert-butylisoxazole</strong> (8.93 g, 63.7 mmol, 1 eq.) in CH2Cl2 (60 mL) was added 4-phenyloxyphenyl isocyanate (15.47 g, 73.3 mmol, 1.15 eq.) dropwise. The mixture was heated at the reflux temp. for 2 days, eventually adding additional CH2Cl2 (80 mL). The resulting mixture was poured into water (500 mL) and extracted with Et2O (3.x.200 mL). The organic layer was dried (MgSO4) then concentrated under reduced pressure. The residue was recrystallized (EtOAc) to give the desired product (15.7 g, 70percent): mp 182-184° C.; TLC (5percent acetone/95percent acetone) Rf 0.27; 1H-NMR (DMSO-d6) delta 1.23 (s, 9H), 6.02 (s, 1H), 6.97 (dd, J=0.2, 8.8 Hz, 2H), 6.93 (d, J=8.8 Hz, 2H), 7.08 (t, J=7.4 Hz, 1H), 7.34 (m, 2H), 7.45 (dd, J=2.2, 6.6 Hz, 2H), 8.80 (s, 1H), 10.04 (s, 1H); FAB-MS m/z (rel abundance) 352 ((M+H)+, 70percent).
70%	In dichloromethane; for 48h;Heating / reflux;	To a solution of <strong>[59669-59-9]5-amino-3-tert-butylisoxazole</strong> (8.93 g, 63.7 mmol, 1 eq.) in CH2Cl2 (60 mL) was added 4-phenyloxyphenyl isocyanate (15.47 g, 73.3 mmol, 1.15 eq.) dropwise. The mixture was heated at the reflux temp. for 2 days, eventually adding additional CH2Cl2 (80 mL). The resulting mixture was poured into water (500 mL) and extracted with Et2O (3 x 200 mL). The organic layer was dried (MgSO4) then concentrated under reduced pressure. The residue was recrystallized (EtOAc) to give the desired product (15.7 g, 70percent): mp 182-184 °C; TLC (5percent acetone/95percent acetone) Rf 0.27; 1H-NMR (DMSO-d6) delta 1.23 (s, 9H), 6.02 (s, 1H), 6.97 (dd, J=0.2, 8.8 Hz, 2H), 6.93 (d, J=8.8 Hz, 2H), 7.08 (t, J=7.4 Hz, 1H), 7.34 (m, 2H), 7.45 (dd, J=2.2, 6.6 Hz, 2H), 8.80 (s, 1H), 10.04 (s, 1H); FAB-MS m/z (rel abundance) 352 ((M+H)+,70percent).

Reference： [1]Patent: US2007/244120,2007,A1 .Location in patent: Page/Page column 24-25
[2]Patent: US2012/46290,2012,A1 .Location in patent: Page/Page column 24
[3]Patent: EP1047418,2005,B1 .Location in patent: Page/Page column 39-40

10
[ 59669-59-9 ]
[ 166964-06-3 ]

Yield	Reaction Conditions	Operation in experiment
64%	With N-Bromosuccinimide;	(a) 5-Amino-4-bromo-3-tert-butylisoxazole 5-Amino-4-bromo-3-tert-butylisoxazole was prepared from <strong>[59669-59-9]5-amino-3-tert-butylisoxazole</strong> and N-bromosuccinimide in 64percent yield as described in Example 1a.
64%	With N-Bromosuccinimide;	(a) 5-Amino-4-bromo-3-tert-butylisoxazole 5-Amino-4-bromo-3-tert-butylisoxazole was prepared from <strong>[59669-59-9]5-amino-3-tert-butylisoxazole</strong> and N-bromosuccinimide in 64percent yield as described in Example 40a.

Reference： [1]Patent: US5514691,1996,A
[2]Patent: US5571821,1996,A

11
[ 59669-59-9 ]
[ 15673-05-9 ]
[ 55809-36-4 ]

Yield	Reaction Conditions	Operation in experiment
52%	With lithium hydroxide; hydroxylamine hydrochloride; In ethanol; water;	EXAMPLE 2 Preparation of 3-amino-5-(t-butyl)isoxazole In a 1 l. 3-neck round bottom flask there was placed 30 g. of pivalyl acetonitrile, 13.5 g. of lithium hydroxide, 394 ml. of water and 281 ml. of ethanol. This mixture was heated to reflux and there was added thereto over a period of 10 minutes 94 ml. of an aqueous solution of 22.2 g. of hydroxylamine hydrochloride. The pH of the reaction mixture after the addition was complete was about 7.3. This pH was adjusted to about pH 6.7 using concentrated aqueous hydrochloric acid. After 30 minutes the pH was about 6.1. After 1 hour the pH was about 6.3. The pH was checked again at 2 hours and at 3 hours after the addition was complete and the pH at those times was about 6.6. A recheck of the pH at 4 hours, 5 hours, and 6 hours revealed the pH to be at about 6.7. The reaction mixture was then refluxed overnight. The following morning the pH was about 6.8. The reaction mixture was cooled and the ethanol removed from the mixture on the rotovapor at room temperature. A solid which separated was filtered off and dried. It weighed 18.65 g. and it was determined by vpc that the product contained 97percent of the desired 3-amino-5-(t-butyl)isoxazole, and 1.6percent of 5-amino-3-(t-butyl)isoxazole. Yield: 52percent of desired isomer.

Reference： [1]Patent: US4259501,1981,A

12
[ 59669-59-9 ]
[ 624-83-9 ]
[ 59669-45-3 ]

Yield	Reaction Conditions	Operation in experiment
	In benzene;	a. Formation of 1-[3-(1,1-dimethylethyl)-5-isoxazolyl]-3-methylurea A 50 milliliter flask with a magnetic stirring bar was charged with 1.3 grams (0.0093 mole) of 3-(1,1-dimethylethyl)-5-isoxazolamine and 25 milliliters of benzene. To this was added 1.7 grams of methyl isocyanate and one (1) drop of triethylamine; and the mixture was allowed to stand overnight, after which it was heated to reflux for 7.5 hours and then allowed to stand at room temperature for two (2) days. Thin layer chromatography showed only partial reaction, so a trace of 4-dimethylaminopyridine and several milliliters of methyl isocyanate were added and the mixture heated at reflux for 4.5 hours. The mixture was then concentrated on a rotary evaporator to give 2.6 grams of a viscous red brown oil. Chromatography on alumina with chloroform/ethyl acetate monitored by TLC gave fractions containing a single component. These fractions were combined and evaporated to give 0.67 gram of a pale yellow solid of 1-[3-(1,1-dimethylethyl)-5-isoxazolyl]-3-methylurea, M.P. 188°-196° C., which showed a molecular ion at 197 in the mass spectrum.

Reference： [1]Patent: US4268679,1981,A

13
[ 59669-59-9 ]
2,6-di-n-propoxybenzoyl chloride [ No CAS ]
N-[3-(1,1-dimethylethyl)-5-isoxazolyl]-2,6-di-n-propoxybenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10%	With triethylamine; In tetrahydrofuran; dichloromethane; water;	(B) To a stirred solution of 2.8 g of 5-amino-3-(1,1-dimethylethyl)isoxazole in 40 ml of tetrahydrofuran containing 4.5 ml of triethylamine was added dropwise over ten minutes a solution of 4.88 g of 2,6-di-n-propoxybenzoyl chloride in 10 ml of tetrahydrofuran. Following the addition, the reaction mixture was heated at reflux for seventy-two hours. The reaction mixture was then cooled to room temperature and the solvent was removed by evaporation under reduced pressure. The residue was dissolved in a mixture of dichloromethane and water, and the organic layer was separated, washed with fresh water, dried, and the solvent was removed by evaporation to provide an oil. The oil was crystallized from Skelly B and diethyl ether to provide 750 mg of N-[3-(1,1-dimethylethyl)-5-isoxazolyl]-2,6-di-n-propoxybenzamide. M.P. 85°-87° C. Yield 10percent. Analysis calculated for C20 H28 N2 O4 Theory: C, 66.64; H, 7.83; N, 7.77. Found: C, 67.65; H, 7.78; N, 7.32.

Reference： [1]Patent: US4416683,1983,A

14
[ 59669-59-9 ]
[ 51708-72-6 ]
[ 92338-90-4 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In ethyl acetate;	A. 4-Chloro-N-[3-(1,1-dimethylethyl)-5-isoxazolyl]-2-methylbutanamide To a stirred solution of 7 g of <strong>[59669-59-9]3-(1,1-dimethylethyl)-5-aminoisoxazole</strong> dissolved in 50 ml ethyl acetate was added 5.05 g of triethylamine at room temperature. As the solution continued to stir, 8 g of 2-methyl-4-chlorobutyric acid chloride was added to the reaction mixture over a 15 minute period. The reaction was allowed to stir for about 3 days and the precipitated triethylamine hydrochloride salt was collected by filtration and washed with ethyl acetate. The solvent was evaporated from the filtrate under reduced pressure and the residue was recrystallized from diethyl ether to afford 4-chloro-N-[3-(1,1-dimethylethyl)-5-isoxazolyl]-2-methylbutanamide as a solid. mp 135°-137° C. Analysis calculated for C12 H19 ClN2 O2: Theory: C, 55.70; H, 7.40; N, 10.83. Found: C, 55.41; H, 7.15; N, 10.84.

Reference： [1]Patent: US4500343,1985,A

15
[ 59669-59-9 ]
[ 7693-46-1 ]
[ 765914-99-6 ]

Yield	Reaction Conditions	Operation in experiment
41%	With pyridine; In dichloromethane;	Step E: (3-tert-Butyl-isoxazol-5-yl)-carbamic acid 4-nitrophenyl ester A solution of 3-tert-butyl-isoxazol-5-ylamine (2.50 g, 17.83 mmol) in dichloromethane was treated with pyridine (2 mL, 26.7 mmol) followed by p-nitrophenyl chloroformate (3.77 g, 18.73 mmol). The mixture was stirred at room temperature for 2 hours. The reaction mixture was washed with 1N HCl, filtered, and concentrated under reduced pressure. The residue was triturated with ether and collected by filtration to afford 2.2 g of product (41percent yield).

Reference： [1]Patent: US2004/192653,2004,A1

16
[ 59669-59-9 ]
[ 327-78-6 ]
bis(4-chloro-3-(trifluoromethyl)phenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; dichloromethane; toluene;	To a solution of <strong>[59669-59-9]5-amino-3-tert-butylisoxazole</strong> (0.100 g) in anh toluene (5 niL) was added 4-chloro-3-(trifluoromethyl)phenyl isocyanate (0.395 g). The reaction vessel was sealed, heated at 85° C. for 24 h, and cooled to room temp. The reaction mixture was added to a slurry of Dowex.(R).50WX2-100 resin (0.5 g) in CH2Cl2 (40 mL), and the resulting mixture was stirred vigorously for 72 h. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (gradient form 100percent CH2Cl2 to 5percent MeOH/95percent CH2Cl2) to give bis(4-chloro-3-(trifluoromethyl)phenyl)urea followed by N-(3-tert-butyl-5-isoxazolyl)-N'-(4-chloro-3-(trifuoromethyl)phenyl)urea.

Reference： [1]Patent: US2004/102636,2004,A1

17
[ 59669-59-9 ]
[ 17341-93-4 ]
[ 908267-38-9 ]

Yield	Reaction Conditions	Operation in experiment
18%	With sodium hydrogencarbonate; In water; ethyl acetate; at 20℃; for 72h;	Step 1: Synthesis of compound F-2. Trichloroethyl chloroformate (1.1 mL, 8.6mmol) is added to a mixture of 1 g (7.1 mmol) of compound F-l and 1.8 g (21.4 mmol) of sodium hydrogen carbonate in ethyl acetate/water (1/1, 20 mL) at room temperature. The resulting mixture is vigourously stirred for 3 d and then additional trichloroethyl chloroformate (1.1 mL, 8.6mmol) and sodium hydrogen carbonate (1.8 g, 21.4 mmol) are added. The mixture is stirred for a further 3 h. The aqueous layer is separated and extracted with ethyl acetate (2 x 25mL). The organic layers are combined, dried over MgS04, filtered and the filtrate isconcentrated under reduced pressure. The residue is purified by column chromatography (silica, eluent: ethyl acetate/heptanes) followed by trituration with heptanes to give 397 mg of compound F-2. Yield: 18percent; ES-MS: m/z 315 [M+H]; *H NMR (250 MHz,CHLOROFORM-if) delta ppm 1.33 (s, 9 H) 4.86 (s, 2 H) 6.11 (s, 1 H) 7.68 (br. s., 1 H)
	With sodium hydrogencarbonate; In water; ethyl acetate; at 0 - 20℃; for 3h;	To a solution of the starting pyrazole amine (1 eq) in EtOAc were added 2,2,2-trichloroethylchloroformate (1.1 eq) and saturated NaHCO3 (2-3 eq) at 0° C. After stirring for 3 h at RT, the layers were separated and the aqueous layer extracted with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated under vacuum to yield the crude TROC carbamate of the pyrazole amine.Example 2To a solution of 2,2,2-trichloroethyl 3-tert-butylisoxazol-5-ylcarbamate (0.080 g, 0.25 mmol), formed via General method B from Example B1, in dioxane (3 mL) was added Example A2 (70 mg, 0.25 mmol) and 1-methylpyrrolidine (22 mg, 0.25 mmol). The reaction mixture was heated overnight at 65° C. The reaction mixture cooled to RT, concentrated in vacuo, DCM (2 mL) was added and the slurry was stirred for 1 hour. The solid was filtered and air dried to obtain 1-(4-(2-(1H-1,2,4-triazol-1-yl)pyridin-4-yloxy)-2-fluorophenyl)-3-(3-tert-butylisoxazol-5-yl)urea. 1H NMR (400 MHz, DMSO-d6): delta 10.3 (s, 1H), 9.56 (s, 1H), 8.70 (s, 1H), 8.34 (s, 1H), 8.29 (d, J=6.0 Hz, 1H), 8.03 (t, J=9.2 Hz, 1H), 7.68 (dd, J=2.0, and 5.6 Hz, 1H), 7.57 (d, J=1.2 Hz, 1H), 7.26 (dd, J=2.8, and 12.0 Hz, 1H), 7.03 (m, 1H), 6.05 (s, 1H), 1.24 (s, 9H); MS (ESI) m/z: 438.1 (M+H+).

Reference： [1]Patent: WO2012/12307,2012,A1 .Location in patent: Page/Page column 47-48
[2]Patent: US2008/261961,2008,A1 .Location in patent: Page/Page column 15; 17

18
[ 75-44-5 ]
[ 59669-59-9 ]
[ 696-63-9 ]
[ 1044665-27-1 ]

Yield	Reaction Conditions	Operation in experiment
36%		A mixture of 4-Methoxy-benzenethiol (0.20g, 1 eq) and potassium carbonate (0.47g, 2.5eq) in dry THF was allowed to stir at room temperature under argon for an hour. Then the stirred suspension was cooled to0 C and to it was added drop wise a solution of phosgene (0.17g1. 2eq). The reaction stirred at0 C for half an hour. Then 3-tert-Butyl-isoxazol-5- ylamine (0.20g, leq) in THF was added dropwise. The reaction was allowed to warm to room temperature and stirred overnight. The solvent was removed and extracted with ethyl acetate and water. The organic layer was dried over magnesium sulfate and solvent removed. It was purified by HPLC. Yield: 157mg (36percent)

Reference： [1]Patent: WO2005/48948,2005,A2 .Location in patent: Page/Page column 214

19
[ 59669-59-9 ]
[ 20469-89-0 ]
2-bromo-N-(3-tert-butyl-isoxazol-5-yl)-2-methyl-propionamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 16h;	The crude acid chloride is redissolved in DCM (300 mL) N5N- diisopropylethylamine (46.9 mL, 0.27 mol) and 3-tert-butyl-isoxazol-5-ylamine (12.6 g, 89.8 mmol) are introduced. The reaction is stirred at room temperature for 16 h. After this time, the mixture is washed with saturated aqueous NaHCO3 solution, brine and the organic layer is separated, dried (Na2SO4) and concentrated under reduced pressure. The crude product is purified by recrystallisation using heptanes/isopropyl alcohol to give the title compound 1(11.0 g, 43percent). IH NMR (400 MHz, CHLOROFORM-d) delta ppm 1.33 (9 H, s), 2.04 (6 H, s), 6.32 (1 H, s), 9.05 (1 H, br s).

Reference： [1]Patent: WO2009/105509,2009,A1 .Location in patent: Page/Page column 38

20
[ 59669-59-9 ]
[ 1203680-02-7 ]
[ 1203680-03-8 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 3-te/t-butyl-isoxazol-5-ylamine (0.421g; 3.00 mmol) in methylene chloride (10 mL) was added dropwise the trimethylaluminum (1.50 mL of a 2.0 M solution in toluene; 3.0 mmol). The mixture was stirred 15 minutes and 3-methyl-3- (tetrahydro-pyran-4-sulfonyl)-dihydro-furan-2-one (0.596 g; 2.40 mmol) was added. The mixture was heated to 45 0C overnight, cooled to room temperature, carefully quenched with 0.5 mL methanol, applied to a plug of silica gel and eluted with ethyl acetate. Removal of the volatiles in vacuo provided a residue which was purified by silica gel chromatography using ethyl acetate and hexanes as the eluent. The product-rich fractions were concentrated in vacuo to provide 0.646 g of the desired product. 1H NMR (CDCI3) 5 9.92 (bs, IH), 6.29 (s, IH), 4.11-3.92 (m, 4H), 3.86 (m, IH), 3.60 (m, IH), 3.40 (m, 2H), 2.57 (m, IH), 2.36 (m, IH), 2.12-1.90 (m, 4H), 1.80 (s, 3H), 1.32 (s, 9H). MS (ESI): m/e 389 (M+H).

Reference： [1]Patent: WO2010/5782,2010,A1 .Location in patent: Page/Page column 33-34

21
[ 59669-59-9 ]
[ 1203679-84-8 ]
[ 1203679-87-1 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 3-te/t-butyl-isoxazol-5-ylamine (0.421 g; 3.00 mmol) in methylene chloride (5 mL) was added dropwise trimethylaluminum (1.5 mL of a 2.0 M solution in toluene; 3.00 mmol). The mixture was stirred 15 minutes and 3-(4-chloro- benzenesulfonyl)-3-methyl-dihydro-furan-2-one (0.659 g; 2.40 mmol) added. The mixture was stirred 3 hours, heated to 45 0C for approximately 40 hours, cooled to room temperature and carefully quenched with 10percent aqueous citric acid, aqueous sodium tartrate and chloroform. The organic layer was dried (MgSO4). Removal of the volatiles in vacuo provided a residue which was purified by silica gel chromatography using ethyl acetate and hexanes as the eluent. Removal of the volatiles from the product-rich fractions provided 0.616 g of the desired product. 1U NMR (CDCl3) delta 9.85 (bs, IH), 7.75 (d, 2H), 7.55 (d, 2H), 6.24 (s, IH), 3.97 (m, IH), 3.85 (m, IH), 2.62 (m, IH), 2.32 (m, IH), 1.65 (s, 3H), 1.32 (s, 9H). MS (ESI): m/e 415, 417 (M+H).

Reference： [1]Patent: WO2010/5782,2010,A1 .Location in patent: Page/Page column 28-29

22
[ 59669-59-9 ]
[ 98-79-3 ]
[ 1234319-38-0 ]

Yield	Reaction Conditions	Operation in experiment
32.7%		Step 1: Synthesis of (S)-5-oxo-pyrrolidine-2-carboxylic acid (3-tert-butyl-isoxazol-5-yl)- amide; To solution of the (S)-5-oxo-pyrrolidine-2-carboxylic acid (6g, 46.47mmol) in tetrahydrofuran (5OmL) is added thionyl chloride (6.75ml, 92.94mmol) and stirred at room temperature for 2-3 hours. The solvent is removed under reduced pressure and the residue is dissolved in tetrahydrofuran (2OmL) and added dropwise to a solution of 3-tert-butyl-isoxazol-5-ylamine (6.514g, 46.47mmol) and diisopropylamine (24.28ml, 139.41mmol) in tetrahydrofuran (5OmL) at room temperature. The reaction is stirred overnight at room temperature then diluted with dichloromethane and washed sequentially with water and saturated brine solution. The organics are dried over sodium sulfate, filtered and solvents removed under vacuum. The crude residue is purified by flash column chromatography eluting with 5-10percent methanol/dichloromethane. The product rich fractions are pooled and evaporated to afford 3.02g title compound, 32.7percent yield. ESI m/z 252=MH+.

Reference： [1]Patent: WO2010/77836,2010,A2 .Location in patent: Page/Page column 166

23
[ 59669-59-9 ]
[ 26250-84-0 ]
[ 1240055-71-3 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In toluene; at 20℃; for 18h;	Amide coupling procedure 2: Synthesis of (S)-2-(3-toer/-Butyl-isoxazol-5-ylcarbamoyl)- piperidine-1-carboxylic acid tert-b\\xiy\\ ester2-Ethoxy-l-ethoxycarbonyl-l,2-dihydroquinoline (445mg; l.deltammol) is added to a solution of (S)-piperidine-2-carboxylic acid (300mg; 1.308mmol) and 5-amino-3-t-butylisoxazole (183.4mg; 1.308mmol) in toluene (4.2mL) at room temperature and the mixture is stirred for 18 hours. After this time, the mixture is concentrated in vacuo. Purification by flash chromatography on silica gel using methanol/methylene chloride provides the title compound, m/z 352 [M+H+].

Reference： [1]Patent: WO2010/96371,2010,A2 .Location in patent: Page/Page column 86-87

24
[ 59669-59-9 ]
[ 1240057-42-4 ]
[ 1240057-41-3 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; trichlorophosphate; at 0℃; for 0.5h;	Step 2: Synthesis of (S)-l-(4-Chloro-phenyl)-6-oxo-piperidine-2-carboxylic acid (3-tert- butyl-isoxazol-5-yl)-amideTo a cold slurry of (S)-l-(4-Chloro-phenyl)-6-oxo-piperidine-2-carboxylic acid (0.2g; 0.788mmol) and <strong>[59669-59-9]5-amino-3-tert-butylisoxazole</strong> (0.11Og; 0.788mmol) in pyridine (0.956mL; 11.820mmol) is added phosphorous oxychloride (O.O88mL; 0.946mmol). The mixture is stirred at O0C for 30 minutes and then diluted with water and extracted with ethyl acetate several times. The organics are combined and washed with water and brine, dried (Na2SO4), filtered and concentrated in vacuo. Purification by preparative HPLC affords title compound, m/z 376 [M+H+].

Reference： [1]Patent: WO2010/96371,2010,A2 .Location in patent: Page/Page column 118-119

25
[ 59669-59-9 ]
[ 2009-81-6 ]
[ 1253696-33-1 ]

Reference： [1]Synthesis,2010,p. 2767 - 2770

26
[ 59997-51-2 ]
[ 59669-59-9 ]
[ 121449-41-0 ]

Reference： [1]Dyes and Pigments,2010,vol. 86,p. 42 - 49

27
[ 59669-59-9 ]
[ 1258443-85-4 ]
[ 1258443-19-4 ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate; In pyridine; at 0℃; for 0.5h;	To a cold slurry of (S)-1-(4-Chloro-phenyl)-4-oxo-azetidine-2-carboxylic acid (0.2g; 1.037mmol) and <strong>[59669-59-9]5-amino-3-tert-butylisoxazole</strong> (0.145g; 1.037mmol) in pyridine (1.258mL; 15.555mmol) is added phosphorous oxychloride (O.l lbetamL; 1.244mmol). The mixture is stirred at O°C for 30 minutes and then diluted with water and extracted with ethyl acetate several times. The organics are combined and washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by preparative HPLC affords title compound, m/z 348 [M+H+]

Reference： [1]Patent: WO2010/147791,2010,A1 .Location in patent: Page/Page column 53-54

28
[ 59669-59-9 ]
[ 1885-14-9 ]
[ 81479-53-0 ]

Yield	Reaction Conditions	Operation in experiment
84%	With triethylamine; In dichloromethane; at 20℃;	To a stirred solution of 3-tert-butylisoxazol-5-amine (1.04 g, 4 mmol) and phenyl carbonochloridate (624 mg, 4 mmol) in DCM (30 mL) was added triethylamine (484 mg, 4.8 mmol) at room temperature. The reaction mixture was stirred at rt for overnight and then diluted with DCM (80 mL). The resulting mixture was washed sequentially with sat aq NaHC03 and brine. The organic layer was separated, dried over MgSC^, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 1 : 10 EtOAc/DCM to afford phenyl 3-tert-butylisoxazol-5-ylcarbamate (871 mg, 84percent) as a white solid. LC- MS (ESI) /n/z 261 (M + H)+.

Reference： [1]Patent: WO2011/22473,2011,A1 .Location in patent: Page/Page column 172
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 1082 - 1105

29
[ 59669-59-9 ]
N-(3-tert-butyl-5-isoxazolyl)-N'-(4-(4-pyridinyl)thiophenyl)urea [ No CAS ]

Reference： [1]Patent: US2012/46290,2012,A1
[2]Patent: EP1047418,2005,B1

30
[ 59669-59-9 ]
[ 1017540-46-3 ]
N-(3-tert-Butyl-isoxazol-5-yl)-2-methyl-2-(tetrahydro-pyran-4-ylmethanesulfonyl)-propionamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 16h;	Step 6: Synthesis of compound B-7Activation of 55.9 g (22.3 mmol) of compound B-6 is achieved by treatment with thionyl chloride (600 mL) at 60 °C for 3 h. The reaction mixture is cooled to room temperature and excess thionyl chloride is removed under reduced pressure.The crude acid chloride is dissolved in DCM (400 mL) and added to a solution of 31.3 g (22.3 mmol) of <strong>[59669-59-9]3-tert-Butyl-isoxazol-5-ylamine</strong> and N,N-diisopropylethylamine (194 mL) in DCM (250mL). The reaction is stirred at room temperature for 16 h. The reaction mixture is diluted with DCM (1350 mL) and washed with saturated aqueous NaHCC>3 solution (1000 mL). The organic layer is dried over Na2S04, filtered and the filtrate is concentrated under reduced pressure. The crude product is purified by dry-flash column chromatography (2 kg silica, eluent: DCM, 0-20percent ethyl acetate). The resulting solid is recrystallised from isopropanol/heptanes (1/1. 2 L), then dried under reduced pressure to afford 80 g of compound B-7 as an off-white powder. Yield 96percent; ES-MS: m/z 373 [M+H]; XH NMR (360 MHz, CHLOROFORM-d) delta ppm 1.35 (9 H, s), 1.41 - 1.55 (2 H, m), 1.74 (6 H, s), 1.82 - 1.91 (2 H, m), 2.29 - 2.52 (1 H, m), 2.92 (2 H, d, 7=6.58 Hz), 3.34 - 3.49 (2 H, m), 3.88 - 4.00 (2 H, m), 6.30 (1 H, s), 9.38 (1 H, s).

Reference： [1]Patent: WO2012/12307,2012,A1 .Location in patent: Page/Page column 36

31
[ 59669-59-9 ]
[ 1356116-25-0 ]

Reference： [1]Patent: WO2012/12307,2012,A1

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