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[ CAS No. 6311-47-3 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Chemical Structure| 6311-47-3

Chemical Structure| 6311-47-3

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Quality Control of [ 6311-47-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 6311-47-3 ]

SDS Specification

Alternatived Products of [ 6311-47-3 ]

Product Details of [ 6311-47-3 ]

CAS No. :	6311-47-3	MDL No. :	MFCD22056128
Formula :	C₁₂H₉BrN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VXYRBUVRDFHDGD-UHFFFAOYSA-N
M.W :	293.12	Pubchem ID :	238696
Synonyms :

Calculated chemistry of [ 6311-47-3 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	72.51
TPSA :	57.85 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.0 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.03
Log Po/w (XLOGP3) :	4.35
Log Po/w (WLOGP) :	4.1
Log Po/w (MLOGP) :	3.64
Log Po/w (SILICOS-IT) :	1.18
Consensus Log Po/w :	3.06

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.72
Solubility :	0.00556 mg/ml ; 0.000019 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.28
Solubility :	0.00154 mg/ml ; 0.00000525 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.19
Solubility :	0.00189 mg/ml ; 0.00000646 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.97

Safety of [ 6311-47-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 6311-47-3 ]

* 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 [ 6311-47-3 ]
Downstream synthetic route of [ 6311-47-3 ]

[ 6311-47-3 ] Synthesis Path-Upstream 1~4

1
[ 321-23-3 ]
[ 62-53-3 ]
[ 6311-47-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	at 110℃;	4-Bromo-2-fluoro-nitrobenzene (5.6 g, 20.9 mmol) and aniline (2.5 g, 72.2 mmol) are added to 50 ml. of anhydrous NMP. The reaction is heated to 1 10 °C overnight. After cooling to room temperature and removing the solvent, the compound is purified via column chromatography (silica, cyclohexane/ethyl acetate 9:1 ) and obtained as an orange solid in 92percent yield (5.7 g). H-NMR (400 MHz, CD₂CI₂): δ = 9.48 (s, 1 H), 8.06 (d, 1 H), 7.46 (t, 2H), 7.30 (t, 4H), 6.89 (d, 1 H).
88%	at 50℃; for 30 h; Inert atmosphere	4-bromo-2-fluoronitrobenzene (1.0 g, 4.3 mmol) and aniline (490 mg, 5.2 mmol) are suspended in 1 -methyl-2-pyrrolidon (2 ml_). The mixture is purged with argon, then heated to 50°C for 15 h. Additional aniline (350 mg, 3.7 mmol) is added to the reaction. The mixture is stirred at 50°C for 15 h. After cooling to room temperature the mixture is diluted with 2 ml. of methanol and 15 ml_ of water. The obtained precipitate is filtered and washed twice with methanol/water-solution (2:1 ). The solid is dried at 60°C under vacuum. The desired product is obtained in 88percent yield (1 .1 g). ¹H-NMR (400 MHz, CD₂CI₂): δ = 6.89 (d, 1 H), 7.32-7.26 (m, 3H), 7.33 (s, 1 H), 7.46 (t, 2H), 8.05 (d, 1 H), 9.47 (s, 1 H).

Reference： [1] Patent: WO2015/14944, 2015, A1, . Location in patent: Page/Page column 115; 116
[2] Patent: WO2015/150203, 2015, A1, . Location in patent: Page/Page column 85
[3] Patent: WO2014/100695, 2014, A1, . Location in patent: Paragraph 00349
[4] Patent: US2015/30588, 2015, A1, . Location in patent: Page/Page column 71
[5] Patent: US9295673, 2016, B2, . Location in patent: Page/Page column 351; 352

2
[ 62-53-3 ]
[ 586-78-7 ]
[ 6311-47-3 ]

Reference： [1] Chemical Communications, 2016, vol. 52, # 45, p. 7237 - 7240

3
[ 51686-78-3 ]
[ 62-53-3 ]
[ 6311-47-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 1, p. 179 - 183

4
[ 610-38-8 ]
[ 62-53-3 ]
[ 6311-47-3 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1898, vol. 303, p. 325
[2] Recueil des Travaux Chimiques des Pays-Bas, 1902, vol. 21, p. 258[3] Recueil des Travaux Chimiques des Pays-Bas, 1908, vol. 27, p. 35 Anm. 2

[ 6311-47-3 ] Synthesis Path-Downstream 1~32

1
[ 6311-47-3 ]
[ 343952-87-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	With tin(II) chloride dihdyrate; In ethanol; ethyl acetate; at 90℃; for 5h;	compound 5 (12.0 g, 41.1 mmol),Tin(II) chloride dehydrate (45.0 g, 205.5 mmol),Ethanol (ethanol, 150 ml), ethyl acetate (ethyl acetate, 150 ml) was used as a solvent, refluxed at 90 C for 5 hours, cooled to room temperature, and added with potassium hydroxide aqueous solution to separate layers.Extracted with ethyl acetate and dried with a rotary concentrator to give a pale pink solid 9.5 g.The yield was 88%.
	With iron; ammonium chloride; In ethanol; water; at 60℃; for 4h;	To a solution of <strong>[6311-47-3]5-bromo-2-nitro-N-phenylaniline</strong> (1.0 g, 3.41 mmol) in EtOH (15 mL) and H20 (15 mL) was added iron powder (1.15 g, 20.5 mmol) and NH4C1 (1.09 g, 20.5 mmol). The mixture was stirred at 60C for 4h. After completion, the reaction mixture was filtered and the filtrate concentrated to remove EtOH. The residue was diluted with water and extracted with EtOAc. The organic layer was concentrated to give the crude diamine product which was used in next step without further purification. LCMS (m/z): 263.1/264.1 [M+H]+/ [M+2H]+

Reference： [1]Patent: CN109516980,2019,A .Location in patent: Paragraph 0035
[2]Justus Liebigs Annalen der Chemie,1898,vol. 303,p. 325
[3]Patent: WO2014/100695,2014,A1 .Location in patent: Paragraph 00350
[4]Patent: WO2014/151147,2014,A1 .Location in patent: Paragraph 00641
[5]Patent: US2015/30588,2015,A1 .Location in patent: Page/Page column 71
[6]Patent: US9295673,2016,B2 .Location in patent: Page/Page column 352

2
[ 610-38-8 ]
[ 62-53-3 ]
[ 6311-47-3 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1898,vol. 303,p. 325

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 80℃; for 18h;	General procedure: A mixture of 4-bromo-2-fluoro-l -nitrobenzene (1.14 g, 1 eq) and aniline (1 eq) in DMF (30 mL) was heated at 80 C and the reaction progression checked by LC MS. After 18 h the reaction was cooled down to room temperature, diluted with water (50 mL) and extracted with DCM (3 x 50 mL). The organic layers were collected, washed with H20 (2 x 50 mL), brine (1 x 50 mL) and dried (MgSC^). The solvent was removed under reduced pressure and the crude product was used in the next reaction without further purification. 1-497, LC MS [M + 1] + m/z 293.00; 1-498, LC MS [M + 1]+ m/z 323.00

5
[ 6311-47-3 ]
[ 96048-75-8 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1898,vol. 303,p. 325
[2]Patent: WO2014/100695,2014,A1
[3]Patent: WO2014/151147,2014,A1
[4]Patent: US2015/30588,2015,A1
[5]Patent: US9295673,2016,B2

6
[ 6311-47-3 ]
2-[(2-anilino-4-bromo-phenylimino)-methyl]-phenol [ No CAS ]

Reference： [1]Justus Liebigs Annalen der Chemie,1898,vol. 303,p. 325

7
[ 51686-78-3 ]
[ 62-53-3 ]
[ 6311-47-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 179 - 183

8
[ 6311-47-3 ]
[ 536-74-3 ]
[ 1116091-02-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 179 - 183

9
[ 6311-47-3 ]
[ 108-49-6 ]
[ 1396780-27-0 ]

Yield	Reaction Conditions	Operation in experiment
	In 1-methyl-pyrrolidin-2-one; at 110℃; for 16h;	Example 41 Synthesis of TRV 1098 and TRV 1099 [00216] Scheme for TRV 1098 and TRV 1099TRV- 1099 When R= CH3,R'=HTRV- 1098 When R,R'= CH3 [00217] Synthesis of (2, 6-dimethyl-4-(4-nitro-3-(phenyl amino) phenyl) piperazin- l-yl) (phenyl) methanone (TRY 1098)TRV 1098[00218] A solution of <strong>[6311-47-3]5-bromo-2-nitro-N-phenylaniline</strong> ( 1.5g, 5.0mmol) and 2, 6- dimethylpiperazine (0.885g, 7.5mmol) in NMP (15mL) was heated to 1 10 C for 16h. The solution whole cooled to rt to which was slowly added H20 (5 mL). The resulting yellow precipitate was filtered, washed with 10 mL of water, dried (high vacuum, 14h) to furnish 5-(3,5-dimethylpiperazin- l -yl)-2-nitro-N-phenylaniline ( l .Og), 65% yield. It was used in next step without further purification[00219] Crude solution of 5-(3,5-dimethylpiperazin- l -yl)-2-nitro-N-phenylaniline ( 1.0 g, 3.06 mmol), benzoyl chloride (0.4 ml, 3.6 mmol) and triethylamine ( 1.27 ml, 9.18 mmol) in 20 ml DCM was stirred at 0 C for 2 hours. The mixture was washed with water (2x10 ml) and dried over anhydrous sodium sulfate before removing the solvents. (2, 6-dimethyl-4-(4-nitro-3-(phenylamino) phenyl) piperazin- l -yl) (Phenyl) methanone TRV 1098 (0.8 g, 68%) was obtained by flash column chromatograph (40% ethyl acetate in hexanes). NMR (500MHz, CDC13): delta 1.28(d,7=10.0Hz,3H), 1.36(d, J=6.0Hz,3H), 3.22(m,2H), 3.58(m,2H), 4.55(bs, 2H), 6.30(dd, J= 2.5, 9.5Hz, 1H), 6.37(d, J= 2.5, Hz, 1H), 7.23(m, 1 H), 7.32(m,3H), 7.39(m, 2H), 7.45(m,5H), 8.18(d, J = 10.0Hz, 1 H), 9.88(s, 1H). HRMS (+ESI) calculated for CasrW^NaC^: 453.1897, Found: 453.1893

Reference： [1]Patent: WO2012/119035,2012,A1 .Location in patent: Page/Page column 73-74

10
[ 6311-47-3 ]
[ 108-49-6 ]
[ 1396778-99-6 ]

Reference： [1]Patent: WO2012/119035,2012,A1

11
[ 321-23-3 ]
[ 62-53-3 ]
[ 6311-47-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	In 1-methyl-pyrrolidin-2-one; at 110℃;	4-Bromo-2-fluoro-nitrobenzene (5.6 g, 20.9 mmol) and aniline (2.5 g, 72.2 mmol) are added to 50 ml. of anhydrous NMP. The reaction is heated to 1 10 C overnight. After cooling to room temperature and removing the solvent, the compound is purified via column chromatography (silica, cyclohexane/ethyl acetate 9:1 ) and obtained as an orange solid in 92% yield (5.7 g). H-NMR (400 MHz, CD2CI2): delta = 9.48 (s, 1 H), 8.06 (d, 1 H), 7.46 (t, 2H), 7.30 (t, 4H), 6.89 (d, 1 H).
92%	In dimethyl sulfoxide; at 130℃; for 16h;	Take 2-fluoro-4-bromonitrobenzene (4-Bromo-2-fluoro-1-nitrobenzene, 10 g,46.1 millimolar), aniline (5.2 grams, 55.3 millimoles),Dimethyl sulfoxide (DMSO, 130 ml) was reacted at 130 C for 16 hours.Return to room temperature and distill off the solvent under reduced pressureExtracted with ethyl acetate and saline solution,The organic layer was dehydrated with anhydrous magnesium sulfate and then dried with a rotary concentrator.The red liquid was obtained in 12.4 g, and the yield was 92%.
88%	In 1-methyl-pyrrolidin-2-one; at 50℃; for 30h;Inert atmosphere;	4-bromo-2-fluoronitrobenzene (1.0 g, 4.3 mmol) and aniline (490 mg, 5.2 mmol) are suspended in 1 -methyl-2-pyrrolidon (2 ml_). The mixture is purged with argon, then heated to 50C for 15 h. Additional aniline (350 mg, 3.7 mmol) is added to the reaction. The mixture is stirred at 50C for 15 h. After cooling to room temperature the mixture is diluted with 2 ml. of methanol and 15 ml_ of water. The obtained precipitate is filtered and washed twice with methanol/water-solution (2:1 ). The solid is dried at 60C under vacuum. The desired product is obtained in 88% yield (1 .1 g). 1H-NMR (400 MHz, CD2CI2): delta = 6.89 (d, 1 H), 7.32-7.26 (m, 3H), 7.33 (s, 1 H), 7.46 (t, 2H), 8.05 (d, 1 H), 9.47 (s, 1 H).

57%	With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 50℃; for 48h;	To a solution of 105 (10 g, 45.5 mmol) and aniline (5.08 g 54.5mmol) in 100 mL NMP, potassium acetate was added (18.8 g, 136.4 mmol). The reaction mixture was stirred for 48 h at 50C. The reaction was diluted with 500 ml of water. The formed residue was filtered off, washed with H20, dried, and washed with an ice-cold mixture of hexane/ Et20 2: 1 to give (5-bromo-2- nitrophenyl)phenylamine (126) (7.63 g, 57%), 1H-NMR (DMSO-d6 , 400 MHz): 9.47 (s, 1H), 8.05 (d, J = 9.2 Hz, 1H), 7.47 (dd, Ji = J2 = 8.0 Hz, 2H), 7.37-7.33 (m, 2H), 7.27 (dd, Ji = J2 =7.6Hz, 1H), 7.16 (d, J = 2.0 Hz, 1H), 7.02 (dd, = 8.8 Hz, J2 = 2.0 Hz),
	With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 60℃; for 4h;	Aniline (930 mg, 10.0 mmol) was added to a solution of DIPEA (1.94 g, 15.0 mmol) and 4-bromo-2-fluoro-l -nitrobenzene (2.2 g, 10.0 mmol) in DMSO (16 mL). The reaction mixture was stirred at 60C for 4h. Upon completion, the mixture was diluted with water (50 mL), and the resulting precipitate collected by filtration, washed with water and dried in vacuo. The crude product was used in next step without further purification. LCMS (m/z): 293.1/294.1 [M+H]+/ [M+2H]+

Reference： [1]Patent: WO2015/14944,2015,A1 .Location in patent: Page/Page column 115; 116
[2]Patent: CN109516980,2019,A .Location in patent: Paragraph 0032
[3]Patent: WO2015/150203,2015,A1 .Location in patent: Page/Page column 85
[4]Patent: WO2017/39791,2017,A1 .Location in patent: Page/Page column 40-41; 65-66
[5]Patent: WO2014/100695,2014,A1 .Location in patent: Paragraph 00349
[6]Patent: US2015/30588,2015,A1 .Location in patent: Page/Page column 71
[7]Patent: US9295673,2016,B2 .Location in patent: Page/Page column 351; 352
[8]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 944 - 954

12
[ 6311-47-3 ]
[ 1616096-79-7 ]

Reference： [1]Patent: WO2014/100695,2014,A1

13
[ 6311-47-3 ]
C₂₀H₁₄N₄O [ No CAS ]

Reference： [1]Patent: WO2014/151147,2014,A1
[2]Patent: US2015/30588,2015,A1
[3]Patent: US9295673,2016,B2

14
[ 6311-47-3 ]
4-dibenzofuran-4-yl-N₂-phenylbenzene-1,2-diamine [ No CAS ]

Reference： [1]Patent: WO2015/14944,2015,A1

15
[ 6311-47-3 ]
4-dibenzofuran-4-yl-N₁-(3,5-dimethylphenyl)-N₂-phenylbenzene-1,2-diamine [ No CAS ]

Reference： [1]Patent: WO2015/14944,2015,A1

16
[ 6311-47-3 ]
5-dibenzofuran-4-yl-1-(3,5-dimethylphenyl)-3-phenylbenzimidazol-3-ium chloride [ No CAS ]

Reference： [1]Patent: WO2015/14944,2015,A1

17
[ 6311-47-3 ]
5-dibenzofuran-4-yl-1-(3,5-dimethylphenyl)-2-methoxy-3-phenyl-2H-benzimidazole [ No CAS ]

Reference： [1]Patent: WO2015/14944,2015,A1

18
[ 100124-06-9 ]
[ 6311-47-3 ]
5-dibenzofuran-4-yl-2-nitro-N-phenylaniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99.8%	With bis(tri-t-butylphosphine)palladium(0); sodium hydroxide; In 1,4-dioxane; for 0.25h;Inert atmosphere;	A 50% solution of sodium hydroxide (3.36 g, 42.0 mmol) and 280 ml of dioxane are mixed together and argon is bubbled through the solution for one hour. 4-Bromo-2-fluoro-nitrobenzene (4.10 g, 14.0 mmol) is added to the mixture. After stirring for 15 minutes under argon flux, bis(tri- t-butylphosphine)palladium(O) (0.25 g, 0.49 mmol) and dibenzofurane-4-boronic acid (5.94 g, 28.0 mmol) are added. After cooling to room temperature, the precipitate is removed by filtration and washed with dioxane, the organic phases collected and the solvent removed to obtain a dark solid. After adding dichloromethane and extracting the solution with water, the organic phases are dried over anhydrous sodium sulfate and the solvent removed. The desired product is obtained after column chromatography (silica, dichloromethane/cyclohexane 1/1 ) as a yellow solid in 99.8% yields (5.32 g). H-NMR (400 MHz, CD2CI2): delta = 9.62 (s, 1 H), 8.33 (d, 1 H), 8.00 (d, 2H), 7.96 (s, 1 H), 7.63-7.36 (m, 9H), 7.31 (d, 1 H), 7.27-7.23 (m, 1 H).

Reference： [1]Patent: WO2015/14944,2015,A1 .Location in patent: Page/Page column 116

19
[ 6311-47-3 ]
C₁₉H₁₈N₂ [ No CAS ]

Reference： [1]Patent: WO2015/150203,2015,A1

20
[ 6311-47-3 ]
C₂₆H₂₄N₂ [ No CAS ]

Reference： [1]Patent: WO2015/150203,2015,A1

21
[ 6311-47-3 ]
C₂₇H₂₃N₂⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Patent: WO2015/150203,2015,A1

22
[ 6311-47-3 ]
C₂₈H₂₆N₂O [ No CAS ]

Reference： [1]Patent: WO2015/150203,2015,A1

23
[ 6311-47-3 ]
[ 16419-60-6 ]
C₁₉H₁₆N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With bis(tri-tert-butylphosphine)palladium(0); sodium hydroxide; In 1,4-dioxane; at 85℃; for 15h;Inert atmosphere;	Intermediate 1 (1 .0 g, 4.3 mmol) is suspended in 10 mL of dioxane and 2.5 ml. of 5N NaOH solution. The mixture is purged with argon. Then 2-methylphenylboronic acid (1.09 g, 7.86 mmol) and Pd[P(fBu)3]2 (75 mg, 0,14 mmol) are added under argon atmosphere. The reaction mixture is heated to 85C and stirred for 15 h. After cooling to room temperature the reaction mixture is filtered over celite and washed with dichloromethane. The combined organic layers are washed with water, dried over anhydrous sodium sulphate and concentrated under vacuum. The residue is purified via column chromatography (silica, eluent: n-hexane/ THF) and the de- sired product is obtained in 93% yield (1 .2 g). 1H-NMR (400 MHz, CD2CI2): delta = 2.24 (s, 3H), 6.76 (d, 1 H), 7.13 (s, 1 H), 7.15 (d, 1 H), 7.18 - 7.26 (m, 4H), 7.31 (d, 2H), 7.40 (t, 2H), 8.22 (d, 1 H), 9.54 (s, 1 H).

Reference： [1]Patent: WO2015/150203,2015,A1 .Location in patent: Page/Page column 85-86

24
[ 62-53-3 ]
[ 586-78-7 ]
[ 6311-47-3 ]

Reference： [1]Chemical Communications,2016,vol. 52,p. 7237 - 7240

25
[ 6311-47-3 ]
[ 105-53-3 ]
C₁₉H₂₀N₂O₆ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 944 - 954

26
[ 6311-47-3 ]
9-(1,2-diphenyl-1H-benzo[d]imidazol-6-yl)-9H-carbazole [ No CAS ]

Reference： [1]Patent: CN109516980,2019,A

27
[ 6311-47-3 ]
[ 1103917-89-0 ]

Reference： [1]Patent: CN109516980,2019,A

28
[ 6311-47-3 ]
[ 74-88-4 ]
(5-bromo-2-nitrophenyl)methyl(phenyl)amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%		To a solution of 126 (7.63 g, 26 mmol) in 90 ml DMF, NaH was added (1.35 g, 33.8 mmol, 60 percent dispersion in oil) at 0C, and the mixture was stirred at 0C for 0.5 h. Mel (3.7 g, 26 mmol) was added and the mixture was stirred at 0C for 2 h. The reaction was quenched by adding a saturated aqueous solution of ammonium chloride and extracted with Et20. The combined organic layers were washed with H20, then with brine, and dried over MgSC>4, filtered, and the filtrate was concentrated. The residue was purified by chromatography on silica gel (hexane:CC :EtOAc, 30: 10: 1) to give (5- bromo-2-nitrophenyl)methyl(phenyl)amine (127) (7.5 g, 93 %), 'H-NMR (DMSO-d5, 400 MHz): 7.83 (d, J = 8.8 Hz, 1H), 7.75 (d, J = 2.0 Hz, 1H), 7.53 (dd, Ji = 8.8 Hz, J2 = 2.0 Hz 1H), 7.20 (dd, Ji = J2 = 8.4 Hz, 2H), 6.87 (d, Ji = J2 = 7.2 1H), 6.76 (d, J = 8Hz, 2H), 3.29 (s, 3H).

Reference： [1]Patent: WO2017/39791,2017,A1 .Location in patent: Page/Page column 40-41; 65-66

29
[ 6311-47-3 ]
[(S)-1-((S)-2-{5-[4-iodo-3-(methylphenylamino)phenyl]-1H-imidazol-2-yl}pyrrolidin-1-carbonyl)-2-methylpropyl]carbamic acid methyl ester [ No CAS ]

Reference： [1]Patent: WO2017/39791,2017,A1

30
[ 6311-47-3 ]
N-methyl-2-nitro-N-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline [ No CAS ]

Reference： [1]Patent: WO2017/39791,2017,A1

31
[ 6311-47-3 ]
methyl {(S)-1-isopropyl-2-[(S)-2-(5-{3-[methyl(phenyl)amino]-4-nitrophenyl}-1H-imidazol-2-yl)pyrrolidin-1-yl]-2-oxoethyl}carbamate [ No CAS ]

Reference： [1]Patent: WO2017/39791,2017,A1

32
[ 6311-47-3 ]
methyl {(S)-2-[(S)-2-(5-{4-amino-3-[methyl(phenyl)amino]phenyl}-1H-imidazol-2-yl)pyrrolidin-1-yl]-1-isopropyl-2-oxoethyl}carbamate [ No CAS ]

Reference： [1]Patent: WO2017/39791,2017,A1

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Ghs Precautionary Statements

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

Ghs Hazard Statements

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