[ CAS No. 1107627-01-9 ] {[proInfo.proName]}

Name: 1107627-01-9|1-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazole|98+%
Brand: Ambeed
SKU: A572090
Rating: 91 (30 reviews)

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

2D 3D

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Quality Control of [ 1107627-01-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1107627-01-9 ]

Product Details of [ 1107627-01-9 ]

CAS No. :	1107627-01-9	MDL No. :	MFCD16995903
Formula :	C₁₄H₁₉BN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HOCIEDFQOUYLSF-UHFFFAOYSA-N
M.W :	258.12	Pubchem ID :	59474691
Synonyms :

Calculated chemistry of [ 1107627-01-9 ]

Physicochemical Properties

Num. heavy atoms :	19
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.5
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	77.47
TPSA :	36.28 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.15 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.43
Log Po/w (WLOGP) :	1.87
Log Po/w (MLOGP) :	1.31
Log Po/w (SILICOS-IT) :	1.32
Consensus Log Po/w :	1.39

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.26
Solubility :	0.143 mg/ml ; 0.000555 mol/l
Class :	Soluble
Log S (Ali) :	-2.83
Solubility :	0.378 mg/ml ; 0.00146 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.08
Solubility :	0.0217 mg/ml ; 0.0000839 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.85

Safety of [ 1107627-01-9 ]

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 [ 1107627-01-9 ]

* 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.

Downstream synthetic route of [ 1107627-01-9 ]

[ 1107627-01-9 ] Synthesis Path-Downstream 1~31

2
[ 1107627-01-9 ]
[ 1616099-18-3 ]
[ 1616096-91-3 ]

Yield	Reaction Conditions	Operation in experiment
8%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 25℃; for 16h; Inert atmosphere;	3 Step 3: l-(3,4-dihydroisoquinolin-2(lH)-yl)-3-((6-(l-methyl-lH-benzo[d]imidazol-6-yl)pyridin- -yl)amino)propan-2-ol To a stirred mixture of l-((6-bromopyridin-2-yl)amino)-3-(3,4-dihydroisoquinolin- 2(lH)-yl) propan-2-ol (130 mg, 0.36 mmol) in dioxane:H20 (15 mL, 2: 1) was added 1- methyl-6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-benzo[d]imidazole (102 mg, 0.396 mmol), Cs2C03 (351 mg ,1.08 mmol) and then Pd(dppf)Cl2 (10 mg). The mixture was degassed with N2 4 times and stirred at 25 °C for 16 hours. The reaction mixture was quenched with water (20 mL), extracted with EA (20 mL x 3). The combined extracts were washed with brine (20 mL), dried over anhydrous Na2S04 and concentrated. The residue was purified by prep-HPLC to afford the title compound (12 mg, 8%). 1HNMR (CH3OD, 400MHz) δ: 8.05 (s, 1H), 7.88-7.87 (m, 2H), 7.83-7.80 (m, 1H), 7.50 (t, J = 8.0, 1H), 7.13- 7.11 (m, 4H), 7.01-7.00 (m, 1H), 6.40 (d, J = 4.0, 1H), 5.00 (s, 1H), 4.45 (br, 1H), 4.11-4.13 (m, 1H), 3.82-3.61 (m, 6H), 3.52-3.45 (m, 1H), 2.91 (s, 3H), 2.81-2.63 (m, 3H). LCMS (m/z): 414.2 [M+H]+

Reference： [1]Current Patent Assignee: EPIZYME, INC. - WO2014/100695, 2014, A1 Location in patent: Paragraph 00362

3
[ 1107627-01-9 ]
[ 1616099-19-4 ]
[ 1616096-92-4 ]

Yield	Reaction Conditions	Operation in experiment
16%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 100℃; for 2h; Inert atmosphere;	2 Step 2: l-(3,4-Dihydroisoquinolin-2(lH)-yl)-3-((4-(l-methyl-lH-benzo[d]imidazol-6- yl)pyridin-2-yl)amino)propan-2-ol A mixture of l-((4-bromopyridin-2-yl)amino)-3-(3,4-dihydroisoquinolin-2(lH)- yl)propan-2-ol (170 mg, 0.47 mmol), l-methyl-6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)-lH-benzo[d]imidazole (177 mg, 0.68 mmol), Pd(dppf)Cl2 (83 mg, 0.11 mmol) and Na2C03 (151 mg, 1.43 mmol) in dioxane/H20 (5/2 mL) was stirred at 100 °C under N2 for 2h. Upon completion, water was added to the mixture which was extracted with DCM. The organic layer was concentrated and purified by pre-HPLC to give the desired title compound (30 mg, yield 16%). 1H NMR (400 MHz, MeOD): δ 8.41 (s, 1H), 7.90 (d, J=6.8 Hz, 2H), 7.78 (d, J=8.0 Hz, 1H), 7.64 (d, J=8.0 Hz, 1H), 7.33-7.19 (m, 4H), 7.04 (d, J=5.6 Hz, 2H), 4.46 (s, 2H), 4.35 (br.s, 1H), 3.98 (s, 3H), 3.66-3.53 (m, 4H), 3.33-3.13 (m, 4H). LCMS (m/z): 414.2 (M+l).
16%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 100℃; for 2h; Inert atmosphere;

Reference： [1]Current Patent Assignee: EPIZYME, INC. - WO2014/100695, 2014, A1 Location in patent: Paragraph 00364
[2]Duncan, Kenneth W.; Rioux, Nathalie; Boriack-Sjodin, P. Ann; Munchhof, Michael J.; Reiter, Lawrence A.; Majer, Christina R.; Jin, Lei; Johnston, L. Danielle; Chan-Penebre, Elayne; Kuplast, Kristy G.; Porter Scott, Margaret; Pollock, Roy M.; Waters, Nigel J.; Smith, Jesse J.; Moyer, Mikel P.; Copeland, Robert A.; Chesworth, Richard [ACS Medicinal Chemistry Letters, 2016, vol. 7, # 2, p. 162 - 166]

4
[ 3934-20-1 ]
[ 1107627-01-9 ]
[ 954279-15-3 ]
[ 1616096-93-5 ]

Yield	Reaction Conditions	Operation in experiment
28 mg	Stage #1: 2,6-Dichloropyrimidine; 1-amino-3-(3,4-dihydroisoquinoline-2(1H)-yl)propan-2-ol With triethylamine In isopropyl alcohol Reflux; Stage #2: 1-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazole With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 120℃; for 0.666667h; Microwave irradiation;	3 Step 3: l-(3,4-Dihydroisoquinolin-2(lH)-yl)-3-((4-(l-methyl-lH-benzo[d]imidazol-6- yl)pyrimidin-2-yl)amino)propan-2-ol To a solution of the crude intermediate mixture in dioxane/H20 (5 mL) was added l-methyl-6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-benzo[d]imidazole (300 mg), Pd(dppf)Cl2 (67 mg, 0.09 mmol) and CS2CO3 (600 mg, 1.84 mmol). The reaction mixture was heated at 120°C under microwave condition for 40 min. The mixture was concentrated to remove the solvents and the residue dissolved in ethyl acetate and washed with water. The separated organic layer was concentrated and the crude product purified by prepare HPLC to give the title compound (28 mg, 5% overall yield) as a white solid. 1HNMR (CH3OD, 400MHz) δ: 8.22-8.20 (m, 2H), 8.15 (s, IH), 7.96-7.94 (m, IH), 7.62 (d, J = 4.6, IH), 7.15-6.92 (m, 5H), 4.22-4.21 (m, IH), 3.97 (s, 2H), 3.81 (s, 3H), 3.66-3.63 (m, IH), 3.53-3.48 (m, IH), 3.12-3.10 (m, 2H), 2.99-2.85 (m, 4H). LCMS (m/z): 415.2 [M+H]+

Reference： [1]Current Patent Assignee: EPIZYME, INC. - WO2014/100695, 2014, A1 Location in patent: Paragraph 00367; 00368

5
[ 1107627-01-9 ]
[ 1394703-31-1 ]
[ 1616096-95-7 ]

Yield	Reaction Conditions	Operation in experiment
13%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 110℃; Inert atmosphere;	2 Step 2: l-(3,4-dihydroisoquinolin-2(lH)-yl)-3-((6-(l-methyl-lH-benzo[d]imidazol-6- yl)pyrazin-2-yl)amino)propan-2-ol To a flask containing l-((6-chloropyrazin-2-yl)amino)-3-(3,4-dihydroisoquinolin- 2(lH)-yl)propan-2-ol (200 mg, 0.6 mmol) in dioxane:H20 (3: 1) was added l-methyl-6- (4,4,5, 5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-benzo[d]imidazole (200 mg, 0.8 mmol), CS2CO3 (2equiv.) and Pd(dppfCl2) (10 mol %). The mixture was degassed 3 times with N2 beforebeing heated at 110 deg C overnight. Upon completion, the solvents were evaporated and residue purified with prep-HPLC to afford the desired target compound (32 mg, yield 13%). 1H NMR (400 MHz, MeOD): δ 8.27 (s, IH), 8.18 (d, J=9.6 Hz, 2H), 7.99 (d, J= 8.8 Hz, IH), 7.86 (s, IH), 7.72 (d, J=8.4 Hz, IH), 7.09-6.99 (m, 3H), 6.87 (d, J=7.6 Hz, IH), 4.21 (br.s, IH), 3.86 (s, 3H), 3.84-3.54 (m, 4H), 2.89-2.66 (m, 6H). LCMS (m/z): 415.2 (M+l).

Reference： [1]Current Patent Assignee: EPIZYME, INC. - WO2014/100695, 2014, A1 Location in patent: Paragraph 00371

6
[ 1107627-01-9 ]
[ 1088176-04-8 ]
[ 1616096-19-5 ]

Yield	Reaction Conditions	Operation in experiment
26%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 120℃; for 0.666667h; Microwave irradiation;	Compound 45 l-(3,4-dihydroisoquinolin-2(lH)-yl)-3-(3-(l-methyl-lH-benzo[d]imidazol-6- yl)phenoxy)propan-2-ol To a solution of l-(3-bromophenoxy)-3-(3,4-dihydroisoquinolin-2(lH)-yl)propan- 2-ol (200 mg, 0.55 mmol) in a mixed solution (Dioxane / H20 = 4 / 1 mL) were added 1- methyl-6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-benzo[d]imidazole (214 mg, 0.83 mmol), Pd(dppf)Cl2 (40 mg ,0.06 mmol) and Cs2C03 (360 mg, 1.10 mmol). The reaction mixture was heated at 120 °C under microwave condition for 40 min. The solvent was removed by concentration and the residue was dissolved in ethyl acetate, washed with water. The separated organic layer was concentrated and the crude product was purified by preparative HPLC separation to give the title compound (60 mg, yield 26%) MS (ESI+) e/z: 414.1 [M+l]+. 1H NMR (MeOD, 400 MHz), ^ ppm: 9.45 (s, 1H), 8.21 (s, 1H), 8.00-7.93 (m, 2H), 7.50-7.24 (m, 7H), 7.10-7.07 (m, 1H), 4.76-4.70 (m, 1H), 4.62-4.49 (m, 2H), 4.24 (s, 3H), 4.22-4.19 (m, 2H), 3.98-3.94 (m, 1H), 3.60-3.51 (m, 3H), 3.41-3.21 (m, 2H).
26%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 120℃; for 0.666667h; Microwave irradiation;

Reference： [1]Current Patent Assignee: EPIZYME, INC. - WO2014/100695, 2014, A1 Location in patent: Paragraph 00322
[2]Duncan, Kenneth W.; Rioux, Nathalie; Boriack-Sjodin, P. Ann; Munchhof, Michael J.; Reiter, Lawrence A.; Majer, Christina R.; Jin, Lei; Johnston, L. Danielle; Chan-Penebre, Elayne; Kuplast, Kristy G.; Porter Scott, Margaret; Pollock, Roy M.; Waters, Nigel J.; Smith, Jesse J.; Moyer, Mikel P.; Copeland, Robert A.; Chesworth, Richard [ACS Medicinal Chemistry Letters, 2016, vol. 7, # 2, p. 162 - 166]

7
[ 1107627-01-9 ]
[ 1616099-16-1 ]
[ 1616096-77-5 ]

Yield	Reaction Conditions	Operation in experiment
34%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 100℃; for 16h; Inert atmosphere;	2 Step2: l-(3,4-dihydroisoquinolin-2(lH)-yl)-3-((3-(l-methyl-lH-benzo[d]imidazol-6- yl)phenyl)amino)propan-2-ol To a stirred mixture of l-((3-bromophenyl)amino)-3-(3,4-dihydroisoquinolin- 2(lH)-yl) propan-2-ol (120 mg, 0.33 mmol) in dioxane:H20 (15 mL, 2: 1) was added 1- methyl-6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-benzo[d]imidazole (93.6 mg, 0.33 mmol), Cs2C03 (323 mg ,0.99 mmol) and then Pd(dppf)Cl2 (10 mg). The mixture was degassed by N2 for 4 times and then stirred at 100 °C for 16 hours. The reaction mixture was quenched with water (30 mL), extracted with EA (30 mL x 3). The combined extracts were washed with brine (30 mL), dried over anhydrous Na2S04 and concentrated. The residue was purified by prep-HPLC to afford the title compound (46 mg, 34%). 1HNMR (CDC13, 400MHz) δ: 7.87 (s, IH), 7.83-7.81 (m, IH), 7.55-7.52 (m, 2H), 7.29-7.25 (m, IH), 7.15-7.10 (m, 3H), 7.04-6.98 (m, 2H), 6.92 (s, IH), 6.66-6.64 (m, IH), 4.18-4.11 (m, IH), 3.89-3.83 (m, 4H), 3.70-3.64 (m, IH), 3.42-3.38 (m, IH), 3.21-3.14 (m, IH), 3.02-2.94 (m, 3H), 2.71-2.61 (m, 3H). LCMS (m z): 413.2 [M+H]+

Reference： [1]Current Patent Assignee: EPIZYME, INC. - WO2014/100695, 2014, A1 Location in patent: Paragraph 00341

8
[ 302800-13-1 ]
[ 1107627-01-9 ]

Reference： [1]Patent: WO2014/100734,2014,A1
[2]Patent: WO2015/200677,2015,A2

9
[ 321-23-3 ]
[ 1107627-01-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: triethylamine / dimethyl sulfoxide / 3 h / 120 °C / Microwave irradiation 2: ammonium chloride; iron; water / ethanol / 4 h / 60 °C 3: toluene-4-sulfonic acid / 4 h / 100 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 3 h / 100 °C
	Multi-step reaction with 4 steps 1: triethylamine / dimethyl sulfoxide / 3 h / 120 °C 2: iron; ammonium chloride / ethanol; water / 4 h / 60 °C / Inert atmosphere 3: toluene-4-sulfonic acid / 4 h / 100 °C 4: [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); potassium acetate / 1,4-dioxane / 3 h / 100 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: EPIZYME, INC. - WO2014/100734, 2014, A1
[2]Current Patent Assignee: EPIZYME, INC. - WO2015/200677, 2015, A2

10
[ 337915-79-4 ]
[ 1107627-01-9 ]

Reference： [1]Patent: WO2014/100734,2014,A1
[2]Patent: WO2015/200677,2015,A2

11
[ 73183-34-3 ]
[ 53484-16-5 ]
[ 1107627-01-9 ]

Yield	Reaction Conditions	Operation in experiment
6 g	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100℃; for 3h;	[00321] To a solution of 6-bromo-l -methyl- lH-benzo[d] imidazole (5 g, 23.8 mmol) in dioxane (60 mL) was added 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (9.1 g, 35.7 mmol), Pd(dppf)Cl2 (0.5 g) and potassium acetate (4.67 g, 47.6 mmol). The reaction mixture was heated at 100 °C for 3 h, cooled and concentrated. The crude reaction mixture was purified by column chromatography. (6 g, yield 98percent) MS (ESI+) e/z: 259.1.
6 g	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); potassium acetate; In 1,4-dioxane; at 100℃; for 3h;Inert atmosphere;	To a solution of <strong>[53484-16-5]6-bromo-1-methyl-1H-benzo[d]imidazole</strong> (5 g, 23.8 mmol) in dioxane (60 mL) was added 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi(1,3,2-dioxaborolane) (9.1 g, 35.7 mmol), Pd(dppf)C12 (0.5 g) and KOAc (4.67 g, 47.6 mmol). The reaction mixture was heated at 100 °C under nitrogen for 3 h until the reaction appeared complete by TLC analysis. The solvent was evaporated and the resulting residue was purified by flash chromatography on Si02 to afford the desired product (6 g, 93percent) as a pale solid. LCMS (m/z): 259.1 (M+1).

Reference： [1]Patent: WO2014/100734,2014,A1 .Location in patent: Paragraph 00321
[2]Patent: WO2015/200677,2015,A2 .Location in patent: Paragraph 00461; 00462

12
[ 1107627-01-9 ]
[ 1616059-85-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / 1,4-dioxane; water / 3 h / 100 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 27 °C 2.2: 16 h

Reference： [1]Current Patent Assignee: EPIZYME, INC. - WO2014/100734, 2014, A1

13
[ 1107627-01-9 ]
[ 1616059-33-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / 1,4-dioxane; water / 3 h / 100 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 27 °C 2.2: 16 h 3.1: methanol / 16 h / Reflux

Reference： [1]Current Patent Assignee: EPIZYME, INC. - WO2014/100734, 2014, A1

14
[ 1107627-01-9 ]
[ 1616059-77-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / 1,4-dioxane; water / 3 h / 100 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 27 °C 2.2: 16 h
	Multi-step reaction with 2 steps 1.1: [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); caesium carbonate / water; 1,4-dioxane / 3 h / 100 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 20 °C 2.2: 16 h

Reference： [1]Current Patent Assignee: EPIZYME, INC. - WO2014/100734, 2014, A1
[2]Current Patent Assignee: EPIZYME, INC. - WO2015/200677, 2015, A2

15
[ 1107627-01-9 ]
[ 1616059-43-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / 1,4-dioxane; water / 3 h / 100 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 27 °C 2.2: 16 h 3.1: methanol / 16 h / 25 °C / Reflux

Reference： [1]Current Patent Assignee: EPIZYME, INC. - WO2014/100734, 2014, A1

16
[ 591-20-8 ]
[ 1107627-01-9 ]
[ 1616059-76-7 ]

Yield	Reaction Conditions	Operation in experiment
92%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 100℃; for 3h;	9.5 Step 5: 3-(l-methyl-lH-benzo[d]imidazol-6-yl)phenol [00322] To a solution of l-methyl-6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH- benzo [d]imidazole (6 g, 23.1 mmol) in dioxane/water (50 mL) was added 3-bromophenol (4.8 g, 27.7 mmol), Pd(dppf)Cl2 (0.3g) and Cs2C03 (15g, 46.2 mmol). The reaction mixture was heated at 100 °C for 3 h, cooled and concentrated. The crude reaction mixture was purified by column chromatography. (4.8 g, yield 92%) MS (ESI+) e/z: 225.1.
92%	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); caesium carbonate In 1,4-dioxane; water at 100℃; for 3h; Inert atmosphere;	5.5 3-(1-methyl-1H-benzo[d]imidazol-6-yl)phenol To a solution of 1 -methyl-6-(4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1 Hbenzo [d]imidazole (6 g, 23.1 mmol) in dioxane/water (50 mL) were added 3-bromophenol (4.8 g, 27.7 mmol), Pd(dppf)C12 (0.3g), and Cs2CO3 (15g, 46.2 mmol). The reaction mixture was heated at 100 °C under nitrogen for 3 h. The solvent was evaporated and residue was purified by flash chromatography on Si02 to afford 3-(1-methyl-1H-benzo[d]imidazol-6- yl)phenol (4.8 g, 92%). LCMS (mlz): 225.1 (M+1).

Reference： [1]Current Patent Assignee: EPIZYME, INC. - WO2014/100734, 2014, A1 Location in patent: Paragraph 00322
[2]Current Patent Assignee: EPIZYME, INC. - WO2015/200677, 2015, A2 Location in patent: Paragraph 00463; 00464

17
[ 1107627-01-9 ]
1-(3-(1-methyl-1H-benzo[d]imidazol-6-yl)phenoxy)-3-(3-phenyl-6,7-dihydro-1H-pyrazolo[4,3-c]pyridin-5(4H)-yl)propan-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); caesium carbonate / water; 1,4-dioxane / 3 h / 100 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 20 °C 2.2: 16 h 3.1: methanol / 16 h / 25 °C / Reflux

Reference： [1]Current Patent Assignee: EPIZYME, INC. - WO2015/200677, 2015, A2

18
[ 1107627-01-9 ]
1-(7,8-dihydro-1,6-naphthyridin-6(5H)-yl)-3-(3-(1-methyl-1H-benzo[d]imidazol-6-yl)phenoxy)propan-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); caesium carbonate / water; 1,4-dioxane / 3 h / 100 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 20 °C 2.2: 16 h 3.1: ethanol / 5 h / 80 °C

Reference： [1]Current Patent Assignee: EPIZYME, INC. - WO2015/200677, 2015, A2

19
[ 1107627-01-9 ]
(2E)-3-(4-chloro-5-fluoropyridin-3-yl)acrylic acid tert-butyl ester [ No CAS ]
(2E)-3-(5-fluoro-4-(1-methyl-1H-benzo[d]imidazol-6-yl)pyridin-3-yl)acrylic acid dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
740 mg	Stage #1: 1-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazole; (2E)-3-(4-chloro-5-fluoropyridin-3-yl)acrylic acid tert-butyl ester With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; CyJohnPhos In 1,2-dimethoxyethane; water at 80℃; for 16h; Inert atmosphere; Stage #2: With trifluoroacetic acid at 10 - 35℃; for 1h; Stage #3: With hydrogenchloride In ethyl acetate	358.A (A) (2E)-3-(5-Fluoro-4-(1-methyl-1H-benz[d]imidazol-6-yl)pyridin-3-yl)acrylic acid dihydrochloride (A) (2E)-3-(5-Fluoro-4-(1-methyl-1H-benz[d]imidazol-6-yl)pyridin-3-yl)acrylic acid dihydrochloride A mixture of (2E)-tert-butyl 3-(4-chloro-5-fluoropyridin-3-yl)acrylate (519.9 mg), 1-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benz[d]imidazole (779.5 mg), 2-(dicyclohexylphosphino)biphenyl (88 mg), Pd2(dba)3 (122 mg), 2 M aqueous cesium carbonate solution (2.5 mL) and DME (15 mL) was stirred under nitrogen atmosphere at 80° C. for 16 hours. The reaction mixture was diluted with ethyl acetate (50 mL) and water (50 mL), and the aqueous layer was extracted with ethyl acetate. The extract was washed with brine and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to obtain a solid (765 mg). A mixture of the obtained solid (whole amount) and TFA (10 mL) was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and a 4 M solution of hydrogen chloride in ethyl acetate (15 mL) was added to the residue. The precipitate was collected by filtration and washed with ethyl acetate to obtain the title compound (740 mg). MS: [M+H]+298.2.

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - US2017/44132, 2017, A1 Location in patent: Paragraph 0564; 0989; 0990

20
[ 1107627-01-9 ]
(2E)-3-(4-chloro-5-fluoropyridin-3-yl)acrylic acid tert-butyl ester [ No CAS ]
(2E)-N-{4-[(3,3-difluoroazetidin-1-yl)methyl]phenyl}-3-[5-fluoro-4-(1-methyl-1H-1,3-benzodiazol-6-yl)pyridin-3-yl]acrylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; CyJohnPhos; caesium carbonate / 1,2-dimethoxyethane; water / 16 h / 80 °C / Inert atmosphere 1.2: 1 h / 10 - 35 °C 2.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 16 h / 10 - 35 °C

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - US2017/44132, 2017, A1

21
[ 1107627-01-9 ]
(2E)-ethyl 3-(4-chloro-5-fluoropyridin-3-yl)acrylate [ No CAS ]
(2E)-3-(5-fluoro-4-(1-methyl-1H-benzo[d]imidazol-6-yl)pyridin-3-yl)acrylic acid dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
740 mg	Stage #1: 1-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazole; (2E)-ethyl 3-(4-chloro-5-fluoropyridin-3-yl)acrylate With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; CyJohnPhos In 1,2-dimethoxyethane; water at 20 - 80℃; for 16h; Inert atmosphere; Stage #2: With hydrogenchloride In water	358.A (2E)-3-(5-Fluoro-4-(1-methyl-1H-benzo[d]imidazol-6-yl)pyridin-3-yl)acrylic acid dihydrochloride In a nitrogen atmosphere, 80 ° C,(2E) -3- (4-chloro-5-fluoropyridin-3-yl) acrylic acid tert-butyl ester (519.9 mg)1-methyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-benzo [d] imidazole (779.5 mg),2- (dicyclohexylphosphino) biphenyl (88 mg),Pd2 (dba) 3 (122 mg),2M aqueous solution of cesium carbonate (2.5 mL) and DME (15 mL) was stirred at room temperature for 16 hours.The reaction mixture was diluted with ethyl acetate (50 mL) and water (50 mL), and the aqueous layer was extracted with ethyl acetate.The extract was washed with brine and dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure.The residue was purified by silica gel column chromatography (NH, ethyl acetate / hexanes) to give the title solid (765 mg).The resulting solid (total) and TFA (10 mL) was stirred at room temperature for 1 hour.The reaction mixture was concentrated under reduced pressure and a 4 M solution of ethyl acetate in hydrogen chloride (15 mL) was added to the residue.The precipitate was collected by filtration and washed with ethyl acetate to give the title compound (740 mg).

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - TW2017/14883, 2017, A Location in patent: Paragraph 0343

22
[ 1107627-01-9 ]
methyl 3-amino-6-chloro-5-(2H-1,2,3-triazol-2-yl)pyrazine-2-carboxylate [ No CAS ]
3-amino-6-(1-methyl-1H-1,3-benzodiazol-6-yl)-5-(2H-1,2,3-triazol-2-yl)pyrazine-2-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36.34%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 100℃; for 16h; Inert atmosphere;	131.1 Step 1. 3-amino-6- (1-methyl-1H-benzo [d] imidazol-6-yl) -5- (2H-1, 2, 3-triazol-2-yl) pyrazine-2-carbox ylic acid A solution of methyl 3-amino-6-chloro-5- (2H-1, 2, 3-triazol-2-yl) pyrazine-2-carboxylate (500 mg, 1.964 nMol, 1 equiv) , 1-methyl-6- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) -1H-1, 3-benzodiazole (608.25 mg, 2.356 nMol, 1.20 equiv) , Pd (dppf) Cl 2 (287.36 mg, 0.393 nMol, 0.2 equiv) and Cs 2CO 3 (2559.16 mg, 7.855 nMol, 4.0 equiv) in dioxane (40 mL) , water (5 mL) was stirred for 16 h at 100 under nitrogen atmosphere. The resulting mixture was extracted with EtOAc (3x40 mL) . The water solution was acidified to pH 6 with HCl (1M) . The precipitated solids were collected by filtration and washed with water (2x10 mL) . This afford 3-amino-6- (1-methyl-1H-1, 3-benzodiazol-6-yl) -5- (2H-1, 2, 3-triazol-2-yl) pyrazine-2-carboxylic acid (240 mg, 36.34%) as a light yellow solid. LCMS: m/z (ESI) , [M+H] + = 337.1. 1H-NMR (300MHz , MeOD-d 4) δ 3.93 (3H, s) , 7.33-7.35 (2H, m) , 7.43-7.46 (1H, m) , 7.82-7.84 (2H, m) , 8.12 (1H, s)

Reference： [1]Current Patent Assignee: DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD. - WO2020/35052, 2020, A1 Location in patent: Page/Page column 229

23
[ 1107627-01-9 ]
8-bromo-7-(4-fluorophenyl)-2-[[(2R)-1-methylpyrrolidin-2-yl]methyl][1,2,4]triazolo[1,5-c]pyrimidin-5-amine [ No CAS ]
(R)-7-(4-fluorophenyl)-8-(1-methyl-1H-benzo[d] imidazol-6-yl)-2-((1-methylpyrrolidin-2-yl)methyl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.4%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane; water at 100℃; for 2h; Inert atmosphere;	104.5 Step 5. (R)-7-(4-fluorophenyl)-8-(1-methyl-1H-benzo [d] imidazol-6-yl)-2-((1-methylpyrrolidin-2-yl) methyl) - [1, 2, 4] triazolo [1, 5-c] pyrimidin-5-amine (Cmpd. 104) To a solution of 1-methyl-6- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) -1H-1,3-benzodiazole (248.40 mg, 0.962 mmol, 3.00 equiv) and 8-bromo-7- (4-fluorophenyl)-2-[[(2R) -1-methylpyrrolidin-2-yl] methyl] - [1, 2, 4] triazolo [1, 5-c] pyrimidin-5-amine (130 mg, 0.321 mmol, 1 equiv) in dioxane (3 mL, 0.034 mmol, 0.11 equiv) and H2O (0.5 mL, 0.028 mmol, 0.09 equiv) were added K 3PO 4 (204.27 mg, 0.962 mmol, 3.00 equiv) and Pd (dppf) Cl 2 (46.94 mg, 0.064 mmol, 0.20 equiv). After stirring for 2 hours at 100°C under a nitrogen atmosphere, the resulting mixture was concentrated under reduced pressure. The residue was purified by Prep-HPLC with the following conditions (Column: XBridge Prep OBD C18 Column 19*250 mm, 5 μm; Mobile Phase A: Water (0.05%NH 3H 2O), Mobile Phase B: ACN ; Flow rate: 20 mL/min; Gradient: 28%B to 39%B in 8 min; 254: 220 nm; t R: 6.75 min) to afford (R)-7-(4-fluorophenyl)-8-(3-methyl-3H-benzo [d] imidazol-5-yl)-2-((1-methylpyrrolidin-2-yl) methyl) - [1, 2, 4] triazolo [1, 5-f] pyrimidin-5-amine (Cmpd. 104) (5 mg, 3.4%) as a white solid. LCMS: m/z (ESI), [M+H] + = 457.4. 1H-NMR (400 MHz, Methanol-d 4) δ 1.68 -1.86 (3H, m), 1.96 -2.05 (1H, m), 2.34 (1H, q), 2.43 (3H, s), 2.75 -2.89 (2H, m), 3.08 -3.19 (1H, m), 3.22 -3.29 (1H, m), 3.88 (3H, s), 6.94 (2H, t), 7.11 (1H, dd), 7.40 -7.47 (2H, m), 7.59 (1H, d), 7.62 (1H, d), 8.17 (1H, s).

Reference： [1]Current Patent Assignee: DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD. - WO2020/52631, 2020, A1 Location in patent: Page/Page column 166

24
[ 1107627-01-9 ]
5-bromo-4-(4-fluorophenyl)-6-methoxypyrimidin-2-amine [ No CAS ]
4-(4-fluorophenyl)-6-methoxy-5-(1-methyl-1H-1,3-benzodiazol-6-yl)pyrimidin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72.2%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane; water at 100℃; for 2h; Inert atmosphere;	103.1 Step 1. 4- (4-fluorophenyl) -6-methoxy-5- (1-methyl-1H-1,3-benzodiazol-6-yl) pyrimidin-2-amine To a solution of 5-bromo-4- (4-fluorophenyl) -6-methoxypyrimidin-2-amine (1000 mg, 3.354 mmol, 1 equiv) and 1-methyl-6- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) -1H-1,3-benzodiazole (1298.81 mg, 5.032 mmol, 1.5 equiv) in dioxane (30 mL) and H2O (6 mL) were added K 3PO 4 (1424.06 mg, 6.709 mmol, 2 equiv) and Pd (dppf) Cl 2 (490.88 mg, 0.671 mmol, 0.2 equiv). After stirring for 2 hours at 100°C under nitrogen atmosphere, the resulting mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluting with CH 2Cl 2/MeOH (10: 1) to afford 4- (4-fluorophenyl) -6-methoxy-5- (1-methyl-1H-1,3-benzodiazol-6-yl) pyrimidin-2-amine (847 mg, 72.2%) as a yellow solid. LCMS: m/z (ESI), [M+H] + = 350.3.

Reference： [1]Current Patent Assignee: DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD. - WO2020/52631, 2020, A1 Location in patent: Page/Page column 162

25
[ 1107627-01-9 ]
4-(4-fluorophenyl)-6-hydrazineyl-5-(1-methyl-1H-benzo[d] imidazol-6-yl)pyrimidin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / water; 1,4-dioxane / 2 h / 100 °C / Inert atmosphere 2: hydrazine / 1,4-dioxane / 3 h / 100 °C

Reference： [1]Current Patent Assignee: DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD. - WO2020/52631, 2020, A1

26
[ 1107627-01-9 ]
(S)-N'-(2-amino-6-(4-fluorophenyl)-5-(1-methyl-1H-benzo[d] imidazol-6-yl)pyrimidin-4-yl)-2-(1-methylpyrrolidin-2-yl)acetohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / water; 1,4-dioxane / 2 h / 100 °C / Inert atmosphere 2: hydrazine / 1,4-dioxane / 3 h / 100 °C 3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD. - WO2020/52631, 2020, A1

27
[ 1107627-01-9 ]
(S)-7-(4-fluorophenyl)-8-(1-methyl-1H-benzo[d] imidazol-6-yl)-2-((1-methylpyrrolidin-2-yl)methyl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / water; 1,4-dioxane / 2 h / 100 °C / Inert atmosphere 2: hydrazine / 1,4-dioxane / 3 h / 100 °C 3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 4: (Z)-trimethylsilyl N-trimethylsilylacetimidate / 2 h / 20 - 110 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD. - WO2020/52631, 2020, A1

28
[ 1107627-01-9 ]
4-amino-3-bromo-1-(2-chlorophenyl)-7-(trifluoromethyl)-1,8-naphthyridin-2(1H)-one [ No CAS ]
[ 74-88-4 ]
1-(2-chlorophenyl)-3-(1-methyl-1H-benzo[d]imidazol-6-yl)-4-(methylamino)-7-(trifluoromethyl)-1,8-naphthyridin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7.3 mg	Stage #1: 4-amino-3-bromo-1-(2-chlorophenyl)-7-(trifluoromethyl)-1,8-naphthyridin-2(1H)-one With sodium hydride In tetrahydrofuran at 0℃; for 1h; Stage #2: iodomethane In tetrahydrofuran at 0 - 25℃; for 16h; Stage #3: 1-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazole In 1,4-dioxane; water monomer at 100℃; for 16h; Inert atmosphere;	20.4 Step 3: 1-(2-Chlorophenyl)-3-(1-methyl-1H-benzo[d]imidazol-6-yl)-4-(methylamino)-7-(trifluoromethyl) )-1,8-Naphthyridin-2(1H)-one (Compound 20) Synthesis A mixture of intermediate 20-2 and intermediate 20-3 (100 mg, 231.15 μmol), intermediate 20-4 (89.50 mg, 346.73 μmol) was dissolved in dioxane (2 mL) and Pd(dppf)Cl was added 2 (16.91 mg, 23.12 μmol), cesium carbonate (150.63 mg, 462.30 μmol) and water (0.5 mL). The reaction solution was stirred at 100°C under nitrogen protection for 16 hours. LC-MS monitoring showed that all the raw materials had reacted completely, and the target product was formed. The reaction solution was extracted three times with ethyl acetate, the organic layer was concentrated to dryness under reduced pressure, and the residue was purified by high performance liquid chromatography ((column: YMC-Actus Triart C18 15030mm5 μm; mobile phase: [A: 0.05% ammonia water ( v/v), B: acetonitrile]; B%: 45%-65%, 11 min)) to give the title compound (7.3 mg).

Reference： [1]Current Patent Assignee: JIANGSU SIMCERE PHARM - WO2021/254529, 2021, A1 Location in patent: Page/Page column 33-34

29
[ 1107627-01-9 ]
3-amino-6,7,7-trimethyl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: coupling reagent / water monomer / 10 h / 80 °C / Inert atmosphere 2: Cs₂CO₃; (2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1’-biphenyl)[2-(2’-amino-1,1’-biphenyl)]palladium(II) methanesulfonate / 1,4-dioxane / 16 h / 110 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: FOSHAN IONOVA BIOTHERAPEUTICS; SHENZHEN IONOVA LIFE SCIENCE - WO2022/63140, 2022, A1

30
[ 1107627-01-9 ]
5-chloro-4-(1-methyl-1H-benzo[d]imidazol-6-yl)-N-(4-(4-methylpiperazin-1-yl)phenyl)pyrimidin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: coupling reagent / water monomer / 10 h / 80 °C / Inert atmosphere 2: Cs₂CO₃; (2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1’-biphenyl)[2-(2’-amino-1,1’-biphenyl)]palladium(II) methanesulfonate / 1,4-dioxane / 16 h / 110 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: FOSHAN IONOVA BIOTHERAPEUTICS; SHENZHEN IONOVA LIFE SCIENCE - WO2022/63140, 2022, A1

31
[ 1107627-01-9 ]
[ 5750-76-5 ]
6-(2,5-dichloropyrimidin-4-yl)-1-methyl-1H-benzo[d]imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44.9%	With coupling reagent In water monomer at 80℃; for 10h; Inert atmosphere;

Reference： [1]Current Patent Assignee: FOSHAN IONOVA BIOTHERAPEUTICS; SHENZHEN IONOVA LIFE SCIENCE - WO2022/63140, 2022, A1 Location in patent: Paragraph 046; 049-050

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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

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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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. 1107627-01-9 ] {[proInfo.proName]}

Quality Control of [ 1107627-01-9 ]

Related Doc. of [ 1107627-01-9 ]

Product Details of [ 1107627-01-9 ]

Calculated chemistry of [ 1107627-01-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1107627-01-9 ]

Application In Synthesis of [ 1107627-01-9 ]

[ 1107627-01-9 ] Synthesis Path-Downstream 1~31

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry