3535-88-4|5-(tert-Butyl)-2-methoxyaniline| Ambeed

CAS No. :	3535-88-4
Formula :	C₁₁H₁₇NO
M.W :	179.26
SMILES Code :	NC1=CC(C(C)(C)C)=CC=C1OC
MDL No. :	MFCD00026299
InChI Key :	DLTLFDQLMFMTRQ-UHFFFAOYSA-N
Pubchem ID :	4176318

Safety of [ 3535-88-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H312-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Application In Synthesis of [ 3535-88-4 ]

* 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 [ 3535-88-4 ]

[ 3535-88-4 ] Synthesis Path-Downstream 1~49

1
[ 50-00-0 ]
[ 3535-88-4 ]
(5-tert-butyl-2-methoxy-anilino)-methanesulfonic acid [ No CAS ]

References: [1],1957,vol. 4,p. 287,290.
Chem.Abstr.,1958,p. 21112.

2
[ 2154-66-7 ]
[ 3535-88-4 ]
[ 101578-50-1 ]

References: [1],1957,vol. 4,p. 287,288, 291.
Chem.Abstr.,1958,p. 21112.

3
[ 91247-60-8 ]
[ 3535-88-4 ]

References: [1],1957,vol. 4,p. 287,288.
Chem.Abstr.,1958,p. 21112.
[2]Tetrahedron Letters,2003,vol. 44,p. 849 - 851.

4
[ 24439-51-8 ]
[ 3535-88-4 ]
[ 22626-59-1 ]

References: [1]Patent: FR1516276,1968,A .
Chem.Abstr.,1969,vol. 70.
Chem.Abstr.,1969,vol. 70.

5
[ 24451-12-5 ]
[ 3535-88-4 ]
[ 22505-17-5 ]

References: [1]Patent: FR1516276,1968,A .
Chem.Abstr.,1969,vol. 70.
Chem.Abstr.,1969,vol. 70.

6
[ 3535-88-4 ]
[ 5397-14-8 ]
[ 22486-56-2 ]

References: [1]Patent: FR1516276,1968,A .
Chem.Abstr.,1969,vol. 70.
Chem.Abstr.,1969,vol. 70.

7
[ 3535-88-4 ]
[ 18522-99-1 ]
[ 22505-48-2 ]

References: [1]Patent: FR1516276,1968,A .
Chem.Abstr.,1969,vol. 70.
Chem.Abstr.,1969,vol. 70.

10
[ 98-54-4 ]
[ 536723-91-8 ]
[ 3535-88-4 ]
4-tert-butyl-2-(5-tert-butyl-2-methoxy-phenylamino)-phenol [ No CAS ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 849 - 851.

11
[ 1846-68-0 ]
[ 3535-88-4 ]
[ 557-20-0 ]
(5-tert-butyl-2-methoxy-phenyl)-(1-ethyl-oct-2-ynyl)-amine [ No CAS ]
(5-tert-butyl-2-methoxy-phenyl)-(1-ethyl-oct-2-ynyl)-amine [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2003,vol. 42,p. 4244 - 4247.

12
1-naphthyl thioisocyanate [ No CAS ]
[ 3535-88-4 ]
N-(5-tert-butyl-2-methoxyphenyl)-N'-(1-naphthyl)thiourea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	In toluene; at 20℃; for 8h;	To a solution of <strong>[3535-88-4]5-tert-butyl-2-methoxyaniline</strong> (0.372 g, 2.07 mmol) in toluene (5 mL) was added 1-naphthyl thioisocyanate (0.384 g, 2.07 mmol) and the resulting mixture was allowed to stir at room temp. for 8 h to produce a precipitate. The solids were separated and sequentially washed with toluene and hexane to give the desired product as an off-white pwoder (0.364 g, 48%): mp 158-160 C; 1H-NMR (DMSO-d6) δ 1.31 (s, 9H), 3.59 (s, 3H), 6.74 (d, J=8.46 Hz, 1H), 7.13 (dd, J=2.21, 8.46 Hz, 1H), 7.53-7.62 (m, 4H), 7.88-7.95 (m, 4H), 8.06-8.08 (m, 1H), 8.09 (br s, 1H); FAB-MS m/z 365 ((M+H)+).
	In toluene;	N-(5-tert-Butyl-2-methoxyphenyl)-N'-(1-naphthyl)thiourea To a solution of <strong>[3535-88-4]5-tert-butyl-2-methoxyaniline</strong> (0.372 g, 2.07 mmol) in toluene (5 mL) was added 1-naphthyl thioisocyanate (0.384 g, 2.07 mmol) and the resulting mixture was allowed to stir at room temp. for 8 h to produce a precipitate. The solids were separated and sequentially washed with toluene and hexane to give the desired product as an off-white pwoder (0.364 g, 48%): mp 158-160 C.; 1H-NMR (DMSO-d6) δ1.31 (s, 9H), 3.59 (s, 3H), 6.74 (d, J=8.46 Hz, 1H), 7.13 (dd, J=2.21, 8.46 Hz, 1H), 7.53-7.62 (m, 4H), 7.88-7.95 (m, 4H), 8.06-8.08 (m, 1H), 8.09 (br s, 1H); FAB-MS m/z 365 ((M+H)+).

References: [1]Patent: EP1449834,2004,A2 .Location in patent: Page 41.
[2]Patent: US2004/102636,2004,A1 .

13
[ 3535-88-4 ]
[ 86-84-0 ]
N-(5-tert-butyl-2-methoxyphenyl)-N'-(1-naphthyl)thiourea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	In toluene; at 20℃; for 8h;Product distribution / selectivity;	C3. General Method of Thiourea Formation by Reaction with a Thioisocyanate ; [] N-(5-tert-Butyl-2-methoxyphenyl)-N'-(1-naphthyl)thiourea: To a solution of <strong>[3535-88-4]5-tert-butyl-2-methoxyaniline</strong> (0.372 g, 2.07 mmol) in toluene (5 mL) was added 1-naphthyl thioisocyanate (0.384 g, 2.07 mmol) and the resulting mixture was allowed to stir at room temp. for 8 h to produce a precipitate. The solids were separated and sequentially washed with toluene and hexane to give the desired product as an off-white pwoder (0.364 g, 48%): mp 158-160 C; 1H-NMR (DMSO-d6) δ 1.31 (s, 9H), 3.59 (s, 3H), 6.74 (d, J=8.46 Hz, 1H), 7.13 (dd, J=2.21, 8.46 Hz, 1H), 7.53-7.62 (m, 4H), 7.88-7.95 (m, 4H), 8.06-8.08 (m, 1H), 8.09 (br s, 1H); FAB-MS m/z 365 ((M+H)+).

References: [1]Patent: EP1042305,2005,B1 .Location in patent: Page/Page column 46; 63.

14
[ 877165-55-4 ]
[ 3535-88-4 ]
[ 877165-74-7 ]

Yield	Reaction Conditions	Operation in experiment
56%	With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In DMF (N,N-dimethyl-formamide); at 20℃;	To a solution of 1-methyl-7-vinyl-1H-indole-2-carboxylic acid (53 mg, 0.26 mmol) in DMF (3 mL) was added 5-tert-butyl-o-anisidine (47 mg, 0.26 mmol), O-(7-azobenzotriazol-1-yl)-N,N,N',N'-tetrauroniumhexafluorophosphate (HATU, 100 mg, 0.26 mmol), triethylamine (80 μL, 0.82 mmol), and 1-hydrxybenzotriazol (HOAT, 10 mg, 0.07 mmol). The resulting mixture was stirred at room temperature overnight. The reaction mixture was then diluted with EtOAc, washed with water, dried with sodium sulfate and concentrated. The crude product was purified Prep-TLC to afford 53 mg (56%) of the desired amide intermediate. To a solution of the above amide intermediate (53 mg, 0.15 mmol) in acetone (2 mL) and water (0.1 mL) was added osmium tetraoxide (2.5 wt % in t-BuOH, 16 μl, 0.01 mmol) and 4-methylmorpholine N-oxide (68 mg, 0.58 mmol). The resulting yellowish mixture was stirred for 2 h. The reaction was quenched by addition of Na2SO3 (100 mg) in water (0.5 mL). The mixture was then extracted with dichloromethane, washed with brine, dried with sodium sulfate and concentrated. The residue was purified by preparative TLC using 5% MeOH-dichloromethane to afford 49 mg (82%) of the diol intermediate. To a suspension of silica gel (0.75 g) in dichloromethane (5 mL) was added a solution of NaIO4 (62 mg, 0.29 mmol) in H2O (0.4 mL) dropwise with vigorously stirring. A solution of the diol intermediate from above (49 mg, 0.12 mmol) in dichloromethane (0.5 mL) was added. The mixture was stirred vigorously for 2 h when TLC indicated that the reaction was complete. The reaction mixture was then filtered and the silica gel was washed with dichloromethane (15 mL). The combined filtrates were dried over Na2SO4 and concentrated to give the desired aldehyde intermediate (35 mg, 80%) as a yellowish foam. To a solution of the above aldehyde intermediate (35 mg, 0.1 mmol) and 1-propionylpiperazine (142 mg, 1.0 mmol) in dichloroethane (0.7 mL) was added acetic acid (0.15 mL). The mixture was stirred at room temperature for 1.5 hr. To this mixture was then added sodium triacetoxyborohydride (106 mg, 0.5 mmol). The mixture was stirred at room temperature overnight and quenched with sat NaHCO3. The mixture was then extracted with dichloromethane, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography to give 45 mg (92%) of the title compound. ESI MS m/z 490.65 [M+H]+.

References: [1]Patent: US2006/46986,2006,A1 .Location in patent: Page/Page column 32-33.

15
[ 284462-39-1 ]
[ 3535-88-4 ]
[ 284462-54-0 ]

Yield	Reaction Conditions	Operation in experiment
	With CDI;	Entry 6: 5-(4-Aminophenoxy)isoindoline-1,3-dione was prepared according to Method A3. According to Method 2d, <strong>[3535-88-4]5-tert-butyl-2-methoxyaniline</strong> was reacted with CDI followed by 5-(4-aminophenoxy)isoindoline-1,3-dione to afford the urea. Entry 7: 4-(1-Oxoisoindolin-5-yloxy)aniline was synthesised according to Method A12.
	With CDI;	Entry 6: 5-(4-Aminophenoxy)isoindoline-1,3-dione was prepared according to Method A3. According to Method 2d, <strong>[3535-88-4]5-tert-butyl-2-methoxyaniline</strong> was reacted with CDI followed by 5-(4-aminophenoxy)isoindoline-1,3-dione to afford the urea. Entry 7: 4-(1-Oxoisoindolin-5-yloxy)aniline was synthesised according to Method A12.

References: [1]Patent: US2003/144278,2003,A1 .
[2]Patent: US2001/11135,2001,A1 .

16
[ 284462-54-0 ]
[ 3535-88-4 ]
[ 284462-56-2 ]

Yield	Reaction Conditions	Operation in experiment
	With CDI;	According to Method 2d, <strong>[3535-88-4]5-tert-butyl-2-methoxyaniline</strong> was reacted with CDI followed by 4-(1-oxoisoindolin-5-yloxy)aniline to afford the urea. Entry 8: 4-(3-N-Methylcarbamoylphenoxy)aniline was synthesised according to Method A13.
	With CDI;	According to Method 2d, <strong>[3535-88-4]5-tert-butyl-2-methoxyaniline</strong> was reacted with CDI followed by 4-(1-oxoisoindolin-5-yloxy)aniline to afford the urea. Entry 8: 4-(3-N-Methylcarbamoylphenoxy)aniline was synthesised according to Method A13.

References: [1]Patent: US2003/144278,2003,A1 .
[2]Patent: US2001/11135,2001,A1 .

17
[ 3535-88-4 ]
4-tert-butyl-2-isocyanato-1-methoxybenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Entry 4: 5-tert-Butyl-2-methoxyaniline was converted to 5-tert-butyl-2-methoxyphenyl isocyanate according to Method B1.
		Entry 4: 5-tert-Butyl-2-methoxyaniline was converted to 5-tert-butyl-2-methoxyphenyl isocyanate according to Method B1.
		Entry 4: 5-tert-Butyl-2-methoxyaniline was converted to 5-tert-butyl-2-methoxyphenyl isocyanate according to Method B 1.

References: [1]Patent: US2003/144278,2003,A1 .
[2]Patent: US2001/11135,2001,A1 .
[3]Patent: US2002/165394,2002,A1 .

18
[ 3535-88-4 ]
[ 98-88-4 ]
[ 68009-75-6 ]

Yield	Reaction Conditions	Operation in experiment
	With aqueous KOH; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ethanol; water; acetone;	Step 1 2.04 g of potassium isothiocyanate is dissolved at 10 C. in 60 mL of acetone. 2.38 mL of benzoyl chloride are carefully added dropwise. The white suspension is refluxed for 10 minutes and cooled at 10 C. Then a solution of 40 mL of acetone and 3.63 mL of <strong>[3535-88-4]5-tert-butyl-2-methoxyaniline</strong> is added. The solution is then refluxed. After 3 hours, 100 mL of ice water is added and the mixture is extracted with 3*80 mL of ethyl acetate. The combined organic phases are dried and evaporated down under reduced pressure. About 9 g of brown substance is obtained which are refluxed with 11.1 mL of 50% aqueous KOH solution in 43 mL of ethanol. After 1 hour the solution is cooled and combined with 40 mL of water. The alcohol is distilled off under reduced pressure. The brown solution is buffered with 40 mL of saturated NH4Cl solution. The product precipitated is suction filtered and dried. 9.5 g of (3-tert-butyl-6-methoxyphenyl)thiourea is obtained as a brown powder.

References: [1]Patent: US2002/169193,2002,A1 .

19
[ 3535-88-4 ]
[ 75060-39-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium iodide; sodium nitrite; In water;	a 4-tert-Butyl-2-iodoanisole A solution of 8 g (0.11 mol) of sodium nitrite in 25 ml of water was added dropwise to a solution of 20 g (0.11 mol) of <strong>[3535-88-4]5-tert-butyl-2-methoxyaniline</strong> in 120 ml of water/conc. HCL (1:1) cooled to 5 C. After stirring at 5 C. for 15 min, a solution of 19.1 g (0.11 mol) of potassium iodide in 25 ml of water was added dropwise and the solution obtained was stirred at RT for 4 h. It was extracted several times with DCM, and the separated organic phase was washed with 10% strength NaHSO3 solution and water, dried over Na2SO4, and concentrated. Chromatographic purification of the residue which remained on SiO2 using EA/heptane (1:40) yielded 27 g of the title compound in the form of a pale red oil. Rf (SiO2, EA/heptane 1:1)=0.86. MS (ESI): m/e=291 (M+H)+

References: [1]Patent: US6350778,2002,B1 .

20
[ 321-14-2 ]
[ 3535-88-4 ]
5-chloro-N-[5-(1,1-dimethyl)ethyl-2-methoxyphenyl]-2-hydroxybenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89.5%		Example 161 5-Chloro-N-[5-(1,1-dimethyl)ethyl-2-methoxyphenyl]-2-hydroxybenzamide (Comopund No. 160). Using 5-chlorosalicylic acid and 5-[(1,1-dimethyl)ethyl]-2-methoxyaniline as the raw materials, the same operation as the example 16 gave the title compound. Yield: 89.5%. 1H-NMR(DMSO-d6): δ 1.28(9H, s), 3.33(3H, s), 7.01(1H, d, J=8.7Hz), 7.05(1H, d, J=9.0Hz), 7.11(1H, dd, J=8.7, 2.4Hz), 7.47(1H, dd, J=9.0, 3.0Hz), 7.99(1H, d, J=3.0Hz), 8.49(1H, d, J=2.4Hz), 10.78(1H, s), 12.03(1H, s).

References: [1]Patent: EP1352650,2003,A1 .

21
[ 89-56-5 ]
[ 3535-88-4 ]
N-[5(1,1-Dimethyl)ethyl-2-methoxyphenyl]-2-hydroxy-5-methylbenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84.7%		Example 179 N-[5(1,1-Dimethyl)ethyl-2-methoxyphenyl]-2-hydroxy-5-methylbenzamide (Comopund No. 178). Using 5-methylsalicylic acid and 5-(1,1 -dimethyl)ethyl-2-methoxyaniline as the raw materials, the same operation as the example 16 gave the title compound. Yield: 84.7%. 1H-NMR(CDCl3): δ 1.35(9H, s), 2.34(3H, s), 3.93(3H, s), 6.86(1H, d, J=8.7Hz), 6.93(1H, d, J=8.4Hz), 7.12(1H, dd, J=8.7, 2.4Hz), 7.24(1H, dd, J=8.4, 1.8Hz), 7.27(1H, brs), 8.48(1H, d, J=2.4Hz), 8.61(1H, brs), 11.95(1H, s).

References: [1]Patent: EP1352650,2003,A1 .

22
[ 3535-88-4 ]
[ 21907-22-2 ]
[(N(H)C6H3(OMe)t-Bu)Ph2Sb(μ-NC6H3(OMe)t-Bu)2SbPh2(N(H)C6H3(OMe)t-Bu)] [ No CAS ]

References: [1]Inorganic Chemistry,2005,vol. 44,p. 5495 - 5500.

23
[ 3535-88-4 ]
[ 551-06-4 ]
N-(5-tert-butyl-2-methoxyphenyl)-N'-(1-naphthyl)thiourea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	In toluene; at 20℃; for 8h;	C3. General Method of Thiourea Formation by Reaction with a Thioisocyanate; N-(5-tert-Butyl-2-methoxyphenyl)-N'-(1-naphthyl)thiourea: To a solution of <strong>[3535-88-4]5-tert-butyl-2-methoxyaniline</strong> (0.372 g, 2.07 mmol) in toluene (5 mL) was added 1-naphthyl thioisocyanate (0.384 g, 2.07 mmol) and the resulting mixture was allowed to stir at room temp. for 8 h to produce a precipitate. The solids were separated and sequentially washed with toluene and hexane to give the desired product as an off-white powder (0.364 g, 48%): mp 158-160 C.; 1H-NMR (DMSO-d6) δ 1.31 (s, 9H), 3.59 (s, 3H), 6.74 (d, J=8.46 Hz, 1H), 7.13 (dd, J=2.21, 8.46 Hz, 1H), 7.53-7.62 (m, 4H), 7.88-7.95 (m, 4H), 8.06-8.08 (m, 1H), 8.09 (br s, 1H); FAB-MS m/z 365 ((M+H)+).

References: [1]Patent: US2008/269265,2008,A1 .Location in patent: Page/Page column 24.

24
[ 929113-03-1 ]
[ 3535-88-4 ]
[ 849404-96-2 ]

Yield	Reaction Conditions	Operation in experiment
27%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 16h;	Compound 19 (1.84 g, 6.57 mmol) was suspended in p-dioxane (16 mL). Lithium hydroxide (0.157g, 6. 57 mmol) in water (16 mL) was added and the reaction stirred at ambient temperature for 16 h. IN HCL (6.57 mL) was added and the solution stirred for 1 h at which point the solvent was evaporated to yield crude free acid which was taken on without further purification (2.03 g, 6.57 mmol, 99% yield). ESI-MS m/z : 267 (M + H) +. This free acid (0.216 g, 0.507 mmol) was mixed with 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride (EDC, 0.107 g, 0.558 mmol), hydroxybenzotriazole hydrate (HOBT, 0. 085 g, 0.558 mmol), and 5-tert-butyl-o-aniside (0.100 g, 0.558 mmol). DMF (3 mL) was added, followed by DIEA (0.486 mL, 2.79 mmol) and the reaction stirred at ambient temperature for 16 h. The reaction was diluted with acetonitrile (3 mL) and the crude mixture purified by reverse-phase preparatory HPLC to afford compound 3 (0.082 g, 0.151 mmol, 27%).'H NMR (400 MHz, CD30D) : 6 1.07 (s, 9 H), 1.27 (m, 2 H), 1.51 (m, 4 H), 1. 99 (s, 3 H), 2.24 (m, 2 H), 3.10 (m, 2 H), 3.63 (s, 3 H), 6.40 (s, 1 H), 6.69 (m, 1 H), 6.91 (m, 1 H), 7.79 (s, 1 H), 8.12 (s, 1 H) ESI-MS nAz : 456 (M + H) +.

References: [1]Patent: WO2005/34840,2005,A2 .Location in patent: Page/Page column 69-70.

25
[ 41280-65-3 ]
[ 3535-88-4 ]
[ 1114569-65-1 ]

References: [1]Organic Letters,2009,vol. 11,p. 895 - 898.

26
[ 4377-33-7 ]
[ 3535-88-4 ]
[ 1130382-43-2 ]

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 3230 - 3245.

27
[ 75-44-5 ]
[ 3535-88-4 ]
4-tert-butyl-2-isocyanato-1-methoxybenzene [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2386 - 2391.

28
[ 690664-27-8 ]
[ 3535-88-4 ]
{2-(4-bromo-phenyl)-8-fluoro-3-[2-methoxy-5-tert-butyl-phenyl]-3,4-dihydro-quinazolin-4-yl}-acetic acid methyl ester [ No CAS ]

References: [1]Patent: WO2004/41790,2004,A1 .Location in patent: Page/Page column 33-34.

29
[ 848144-33-2 ]
[ 3535-88-4 ]
[ 1041050-80-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 4819 - 4824.

30
[ 848144-33-2 ]
[ 3535-88-4 ]
N-(5-tert-butyl-2-methoxy-phenyl)-2-[4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl]-2-oxo-acetamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 4819 - 4824.

31
[ 3535-88-4 ]
[ 1307815-45-7 ]

Yield	Reaction Conditions	Operation in experiment
	With 4-methyl-morpholine; potassium carbonate; In dichloromethane;	After 10 minutes, 5-tert-Butyl-o-anisidine (1.22 g, in methylene chloride) was added, followed by 1 ml of N-methylmorpholine and the mixture was stirred at room temperature. After 3 hours, the mixture was diluted with 20 ml of methylene chloride and washed with 50 ml of 10% potassium carbonate. The organic layer was concentrated to 30 ml and diluted with 30 ml of hexanes, then chilled to -20 C. overnight. The resulting solids were collected by filtration and washed with hexanes, 10 ml, then air dried to give 2.56 g N-(5-tert-butyl-2-methoxyphenyl)-2-[4-(2-chloroethoxy)naphthalen-1-yl]-2-oxoacetamide as a yellow solid. MS negative ion (M-1)=438, positive ion (M+1)=440. 1H NMR (500 mHz, CDCl3): 9.68, 1H, s; 8.82, 1H, J=8.5, d; 8.63, 1H, J=2.4, d; 8.6, 1H, J=8.4, d; 8.41, 1H, J1=0.8, J2=8.4, dd; 7.68, 1H, m; 7.58, 1H, m; 7.15, 1H, J1=2.4, J2=8.6, dd; 6.88, 1H, J=8.6, d; 6.86, 1H, J=8.4, d; 4.51, 2H, J=5.7, t; 4.01, 2H, J=5.7, t; 3.93, 3H, s; 1.35, 9H, s.

References: [1]Patent: US2011/117055,2011,A1 .

32
[ 3535-88-4 ]
1-(5-(tert-butyl)-2-methoxyphenyl)-3-(4-((2-((3-methoxy-5-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)phenyl)amino)pyrimidin-4-yl)oxy)naphthalen-1-yl)urea [ No CAS ]

References: [1]Patent: US2014/296208,2014,A1 .

33
[ 3535-88-4 ]
[ 1885-14-9 ]
phenyl (5-(tert-butyl)-2-methoxyphenyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.53 g	With sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane;	Phenyl chloroformate (1.40 mL, 11.16 mmol) was added to a stirred solution of 5-(tert-butyl)-2-methoxyaniline (2.00 g, 11.16 mmol) and NaHCO3 (1.90 g, 22.62 mmol) in THF (20 mL) and DCM (20 mL). The mixture was stirred overnight then diluted with water (40 mL) and DCM (20 mL) then passed through a phase-sep cartridge. The resulting filtrate was concentrated in vacuo to afford the sub-title compound (3.53 g) as a red-brown oil. 1H NMR (DMSO-d6) 400 MHz, δ: 9.04 (s, 1H), 7.68 (s, 1H), 7.40-7.44 (m, 2H), 7.19-7.27 (m, 3H), 7.14 (dd, 1H), 6.98 (d, 1H), 3.82 (s, 3H), 1.25 (s, 9H).
3.53 g	With sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane;	Phenyl chloroformate (1.40 mL, 11.16 mmol) was added to a stirred solution of 5-(tert-butyl)-2-methoxyaniline (2.00 g, 11.16 mmol) and NaHCO3 (1.90 g, 22.62 mmol) in THF (20 mL)and DCM (20 mL). The mixture was stirred overnight then diluted with water (40 mL) and DCM (20 mL) then passed through a phase-sep cartridge. The resulting filtrate was concentrated in vacuo to afford the sub-title compound (3.53 g) as a red-brown oil.1H NMR (DMSO-d6) 400 MHz, O: 9.04 (5, 1H), 7.68 (5, 1H), 7.40-7.44 (m, 2H), 7.19-7.27 (m, 3H), 7.14 (dd, 1H), 6.98 (d, 1H), 3.82 (5, 3H), 1.25 (5, 9H).

References: [1]Patent: US2014/296208,2014,A1 .Location in patent: Paragraph 0684; 0685.
[2]Patent: WO2014/162126,2014,A1 .Location in patent: Page/Page column 63; 64.

34
[ 3535-88-4 ]
[ 88-65-3 ]
2-bromo-N-(5-tert-butyl-2-methoxyphenyl)benzamide [ No CAS ]