[ CAS No. 58442-17-4 ]

Name: 58442-17-4|1H-Benzimidazole-5-carbaldehyde|97%
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Quality Control of [ 58442-17-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 58442-17-4 ]

Product Details of [ 58442-17-4 ]

CAS No. :	58442-17-4	MDL No. :	MFCD08741423
Formula :	C₈H₆N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ALCHVVTYAHQOFY-UHFFFAOYSA-N
M.W :	146.15	Pubchem ID :	10012038
Synonyms :

Calculated chemistry of [ 58442-17-4 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	41.48
TPSA :	45.75 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.29 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.63
Log Po/w (XLOGP3) :	1.27
Log Po/w (WLOGP) :	1.38
Log Po/w (MLOGP) :	0.35
Log Po/w (SILICOS-IT) :	2.17
Consensus Log Po/w :	1.16

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.09
Solubility :	1.2 mg/ml ; 0.00821 mol/l
Class :	Soluble
Log S (Ali) :	-1.83
Solubility :	2.16 mg/ml ; 0.0148 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.84
Solubility :	0.213 mg/ml ; 0.00146 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.09

Safety of [ 58442-17-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302+H312+H332-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 58442-17-4 ]

* 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.

Upstream synthesis route of [ 58442-17-4 ]
Downstream synthetic route of [ 58442-17-4 ]

[ 58442-17-4 ] Synthesis Path-Upstream 1~2

1
[ 58442-17-4 ]
[ 74-88-4 ]
[ 181867-19-6 ]
[ 279226-70-9 ]

Reference： [1] European Journal of Medicinal Chemistry, 2018, vol. 158, p. 167 - 183

2
[ 58442-17-4 ]
[ 74-88-4 ]
[ 181867-19-6 ]
[ 279226-70-9 ]

Reference： [1] European Journal of Medicinal Chemistry, 2018, vol. 158, p. 167 - 183

[ 58442-17-4 ] Synthesis Path-Downstream 1~49

1
[ 17626-40-3 ]
[ 58442-17-4 ]
[ 167959-13-9 ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3638 - 3644

2
[ 106429-29-2 ]
[ 58442-17-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With manganese(IV) oxide; In dichloromethane; ethyl acetate; at 20℃; for 72h;	The carboxylic acid V (10.0 g, 56.8 mmol) was dissolved in ethanol (100 mL) and catalytic amount of H2SO4 was added. The solution was then refluxed for 24 h, cooled to room temperature and neutralized with saturated NaHCO3 solution. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3×20 mL). The organic layers were combined, dried over Na2SO4 and concentrated under vacuo on a rotary evaporator to obtain the ester W as a yellowish solid (11.43 g, 99%). Without further purification, the ester (11.43 g, 56.0 mmol) was dissolved in anhydrous THF (100 mL) and cooled to 0 C. under a steady flow of N2. Next, LiAlH4 (3.4 g, 90.2 mmol) was added to the solution and stirred at room temperature for 24 h. After cooling the solution to 0 C., the reaction was quenched by the addition of methanol, NH4Cl, Rochelle's salt and filtered through a whatman filter paper (grade 8). The filtrate was concentrated under vacuo on a rotary evaporator to obtain the desired product as a light brown solid (7.99 g, 96%). The alcohol (7.99 g, 53.9 mmol) was dissolved in CH2Cl2 (200 mL) and MnO2 (19.8 g, 227.6 mmol). The mixture was then stirred at room temperature for 72 h and filtered through a whatman filter paper (grade 8). The filtrate was concentrated under vacuo on a rotary evaporator to obtain the desired aldehyde as a light brown solid (7.5 g, 95%
90%	With manganese(IV) oxide; In methanol; at 20℃; for 48h;	General procedure: 4.94?g (56.7?mmol) of MnO2 were added to a solution of 1.40?g (9.45?mmol) of 7 in 50?mL of MeOH. After 48?h?at rt, the mixture was filtered over silica and by evaporation 1.24?g (90%) of compound 8 was isolated.
41%	With manganese(IV) oxide; In benzene; at 20℃; for 12h;	b) (lH-benzo[d]imidazole-5-carbaldehyde); To a stirring solution of (lH-benzo[d]imidazol-5-yl)methanol (501 mg, 3.38 mmol) in benzene (35 mL) was added MnO2 (2.35, 27.0 mmol). After stirring at room temperature for 12 h the reaction was then filtered through celite and the filter cake was washed with THF (200 mL). The Filtrate was concentrated to give the title compound (IH- benzo[d]imidazole-5-carbaldehyde)(201 mg, 41%) as a white solid: 1H NMR (400 MHz, OMSOd6) delta 12.90 (bs,lH), 10.04 (s, IH), 8.43 (s, IH), 8.19 (s,lH), 7.75 (s, 2H).

20.3%	With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In dichloromethane; at 20℃; for 72h;Molecular sieve;	(1H-benzo[d]imidazole-5-yl)methanol (2.8 mmol, 1 eq.) was dissolved in 30 mL dichloromethane and a molecular sieve (4 ) was added. To the solution were added Tetrapropylammonium perruthenate (0.28 mmol, 0.1 eq.) and N-Methylmorpholine-N-Oxide (9.8 mmol, 3.5 eq.). After stirring the mixture for 72 hours at room temperature 50 mL of ether was added and filtrated. The solvent was removed under reduced pressure and the product was purified by means of flash-chromatography using silica gel and a ethyl acetate/MeOH-gradient.Yield: 0.08 g (20.3%)
20.3%	With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In dichloromethane; at 20℃; for 72h;Molecular sieve;	(1H-benzo[d]imidazole-5-yl)methanol (2.8 mmol, 1 eq.) was dissolved in 30 mL dichloromethane and a molecular sieve (4 A) was added. To the solution were added Tetrapropylammonium perruthenate (0.28 mmol, 0.1 eq.) and N-Methylmorpholine-N-Oxide (9.8 mmol, 3.5 eq.). After stirring the mixture for 72 hours at room temperature 50 mL of ether was added and filtrated. The solvent was removed under reduced pressure and the product was purified by means of flash-chromatography using silica gel and a ethyl acetate/MeOH-gradient.Yield: 0.08 g (20.3%)

Reference： [1]Patent: US2014/309427,2014,A1 .Location in patent: Paragraph 0163; 0164
[2]European Journal of Medicinal Chemistry,2018,vol. 158,p. 167 - 183
[3]Journal of Medicinal Chemistry,2005,vol. 48,p. 5823 - 5836
[4]Patent: WO2007/53131,2007,A2 .Location in patent: Page/Page column 182
[5]Patent: US2008/262063,2008,A1 .Location in patent: Page/Page column 28-29
[6]Patent: US2008/267911,2008,A1 .Location in patent: Page/Page column 36
[7]Journal of Medicinal Chemistry,1995,vol. 38,p. 3638 - 3644

Yield	Reaction Conditions	Operation in experiment
		Step B 1H-benzoimidazole-5-carboxaldehyde To a solution of 1H-benzoimidazole-5-carboxylic acid N,N-methoxy,methyl amide (458 mg in a mixture of 5 mL diethyl ether and 10 mL tetrahydrofuran) at -78 C. was added 3.7 mL of a 1.5M solution of diisobutylaluminum hydride in toluene and the mixture stirred at low temperature. After 1 hour the reaction mixture was cannulated into a 1M solution of sodium potassium tartrate at 0 C. The resulting slurry was stirred vigorously for 2 hours at room temperature after which time it was extracted with ethyl acetate. The organics were washed with water, dried over sodium sulfate and concentrated in vacuo to provide the crude title compound (250 mg).
		Aldehyde preparation: The aldehyde was prepared according to: Talaty, C. N.; Zenker, N.; [CALLERY,] P. S. J. Heterocyclic Chem. 1976, [13,] [1121.] Data [: 1H NMR (DMSO-D6) No. 12. ]89 (bs, 1H), 10.02 (s, 1H), 8.43 (s, 1H), 8.17 (m, 1H), 7.73 (m, 2H).

4
[ 4887-88-1 ]
[ 141-53-7 ]
[ 58442-17-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 827 - 832

5
[ 58442-17-4 ]
[ 223684-20-6 ]
1-(2-aza-bicyclo[2.2.2]oct-2-yl)-2-[3-{2-[(1H-benzoimidazol-5-ylmethyl)-amino]-1-methyl-ethyl}-2-(3,5-dimethyl-phenyl)-1H-indol-5-yl]-2-methyl-propan-1-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 827 - 832

6
[ 58442-17-4 ]
1H-1,3-benzimidazole-5-carbaldehyde oxime [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 5823 - 5836

7
[ 15788-16-6 ]
[ 58442-17-4 ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 5823 - 5836
[2]Journal of Medicinal Chemistry,1995,vol. 38,p. 3638 - 3644
[3]European Journal of Medicinal Chemistry,2018,vol. 158,p. 167 - 183

8
[ 58442-17-4 ]
1-(1H-benzoimidazol-5-ylmethyl)-3-(4-tert-butyl-benzyl)-thiourea [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 5823 - 5836

9
[ 58442-17-4 ]
(1H-benzo[d]imidazol-5-yl)methanamine hydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 5823 - 5836

10
[ 875-51-4 ]
[ 58442-17-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 827 - 832

11
[ 1575-37-7 ]
[ 58442-17-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 827 - 832

12
[ 58442-17-4 ]
[ 167959-20-8 ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3638 - 3644

13
[ 58442-17-4 ]
1H,3'H,3''H-[2,5';2',5'']Terbenzoimidazole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3638 - 3644

14
[ 58442-17-4 ]
5-Propyl-1H,3'H,3''H-[2,5';2',5'']terbenzoimidazole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3638 - 3644

15
[ 58442-17-4 ]
1H,3'H,3''H-[2,5';2',5'']Terbenzoimidazole-5-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3638 - 3644

16
[ 58442-17-4 ]
5-Phenyl-1H,3'H,3''H-[2,5';2',5'']terbenzoimidazole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3638 - 3644

17
[ 58442-17-4 ]
5-Pyridin-2-yl-1H,3'H,3''H-[2,5';2',5'']terbenzoimidazole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3638 - 3644

18
[ 58442-17-4 ]
5-Pyridin-3-yl-1H,3'H,3''H-[2,5';2',5'']terbenzoimidazole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3638 - 3644

19
[ 58442-17-4 ]
5-Pyridin-4-yl-1H,3'H,3''H-[2,5';2',5'']terbenzoimidazole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3638 - 3644

20
Å molecular sieves [ No CAS ]
[ 75-09-2 ]
[ 7529-22-8 ]
[ 15788-16-6 ]
[ 875-51-4 ]
[ 58442-17-4 ]

Yield	Reaction Conditions	Operation in experiment
452 mg (32%, 2 steps)	With LiAlH4; tetrapropylammonium perruthennate; In tetrahydrofuran; N,N-dimethyl-formamide;	EXAMPLE 5 5-Formylbenzimidazole (18) A suspension of 5-benzimidazolecarboxylic acid (1.57 g, 9.7 mmol) in dry THF (50 ml) was cooled to -78 C. under N2, and treated with LiAlH4 (736 mg, 19.4 mmol). After the addition, the mixture was allowed to warm slowly to room temperature and then stirred at r.t. overnight. The mixture was quenched by MeOH and H2 O cautiously, and passed through a short silica gel column eluding with 10% MeOH/EtOAc. The elude was concentrated to give 876 mg crude alcohol as a solid. The crude alcohol (876 mg) was dissolved in a mixture of DMF (3 ml), THF (10 ml) and CH2 Cl2 (40 ml). 4-Methylmorpholine N-oxide (2.25 g, 19.2 mmol), 4 A molecular sieves (5 g), and TPAP (169 mg, 0.48 mmol) were subsequently added to the crude alcohol solution. The mixture was stirred at room temperature overnight, and filtered through a pad of silica gel eluding with 10% MeOH/EtOAc. The elute was concentrated and further purified by flash chromatography on silica gel eluding with 0-10% MeOH/EtOAc to give 452 mg (32%, 2 steps) of 17 as a white solid: mp 164-166 C.; IR (KBr) 3087, 2818, 1690, 1292; 1 H NMR (CD3 OD) delta9.95 (1H, s), 8.34 (1H, s), 8.08 (1H, d, J=1.5), 7.74 (1H, dd, J=8.4, 1.5), 7.63 (1H, d, J=8.4); 13 C NMR (CD3 OD) delta194.2, 146.0, 143.0, 139.8, 133.6, 124.9, 120.7, 116.6; Anal. Calcd for C8 H6 N2 O: C, 65.75; H, 4.14; N, 19.17. Found: C, 65.60; H, 4.17; N, 19.08.

Reference： [1]Patent: US5770617,1998,A

21
[ 75-09-2 ]
[ 7529-22-8 ]
[ 15788-16-6 ]
[ 875-51-4 ]
[ 58442-17-4 ]

Yield	Reaction Conditions	Operation in experiment
452 mg (32%, 2 steps)	With LiAlH4; tetrapropylammonium perruthennate;silica gel; In tetrahydrofuran; N,N-dimethyl-formamide;	EXAMPLE 5 5-Formylbenzimidazole (18) A suspension of 5-benzimidazolecarboxylic acid (1.57 g, 9.7 mmol) in dry THF (50 ml) was cooled to -78 C. under N2, and treated with LiAlH4 (736 mg, 19.4 mmol). After the addition, the mixture was allowed to warm slowly to room temperature and then stirred at r.t. overnight. The mixture was quenched by MeOH and H2 O cautiously, and passed through a short silica gel column eluding with 10% MeOH/EtOAc. The elude was concentrated to give 876 mg crude alcohol as a solid. The crude alcohol (876 mg) was dissolved in a mixture of DMF (3 ml), THF (10 ml) and CH2 Cl2 (40 ml). 4-Methylmorpholine N-oxide (2.25 g, 19.2 mmol), 4A molecular sieves (5 g), and TPAP (169 mg, 0.48 mmol) were subsequently added to the crude alcohol solution. The mixture was stirred at room temperature overnight, and filtered through a pad of silica gel eluding with 10% MeOH/EtOAc. The elute was concentrated and further purified by flash chromatography on silica gel eluding with 0-10% MeOH/EtOAc to give 452 mg (32%, 2 steps) of 17 as a white solid: mp 164-166 C.; IR KBr) 3087, 2818, 1690, 1292; 1 H NMR (CD3 OD) delta 9.95 (1H, s), 8.34 (1H, s), 8.08 (1H, d, J=1.5), 7.74 (1H, dd, J=8.4, 1.5), 7.63 (1H, d, J=8.4); 13 C NMR (CD3 OD) delta 194.2, 146.0, 143.0, 139.8, 133.6, 124.9, 120.7, 116.6; Anal. Calcd for C8 H6 N2 O: C, 65.75; H, 4.14; N, 19.17. Found: C, 65.60; H, 4.17; N, 19.08.

Reference： [1]Patent: US5767142,1998,A

22
[ 40467-01-4 ]
[ 58442-17-4 ]
3-(1H-benzoimidazol-5-yl)-acrylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran;	Step C 3-(1H-benzoimidazol-5-yl)-acrylic acid methyl ester To a solution of <strong>[58442-17-4]1H-benzoimidazole-5-carboxaldehyde</strong> (250 mg in 12 mL dry tetrahydrofuran) at 0 C. was added 1.43 g methyl(triphenylphosphoranylidene)acetate and the mixture allowed to warm to room temperature. After 24 hours the mixture was concentrated in vacuo and purified by flash chromatography on silica gel (methylene chloride:methanol, 93:7) to give the title compound (257 mg).

Reference： [1]Patent: US5849764,1998,A

23
[ 58442-17-4 ]
[ 865878-73-5 ]

Yield	Reaction Conditions	Operation in experiment
96.5%	With hydroxylamine; sodium acetate; In methanol; at 20℃; for 1h;	<strong>[58442-17-4]1H-benzo[d]imidazole-5-carbaldehyde</strong> (0.57 mmol, 1 eq.) was dissolved in 5 mL methanol, hydroxylamine (0.68 mmol, 1.2 eq.) and sodium acetate trihydrate (0.68 mmol, 1.2 eq.) were added. The mixture was stirred for 1 hour at ambient temperature. 20 mL Ethyl acetate was added and the organic layer was washed with 20 mL of brine. The organic layer was dried over magnesium sulfate, filtrated and the solvent was removed under reduced pressure. The product was purified by means of flash-chromatography using silica gel and a ethyl acetate/MeOH-gradient.Yield: 0.09 g (96.5%)
96.5%	With hydroxylamine; sodium acetate; In methanol; at 20℃; for 1h;	<strong>[58442-17-4]1H-benzo[d]imidazole-5-carbaldehyde</strong> (0.57 mmol, 1 eq.) was dissolved in 5 mL methanol, hydroxylamine (0.68 mmol, 1.2 eq.) and sodium acetate trihydrate (0.68 mmol, 1.2 eq.) were added. The mixture was stirred for 1 hour at ambient temperature. 20 mL Ethyl acetate was added and the organic layer was washed with 20 mL of brine. The organic layer was dried over magnesium sulfate, filtrated and the solvent was removed under reduced pressure. The product was purified by means of flash-chromatography using silica gel and a ethyl acetate/MeOH-gradient.Yield: 0.09 g (96.5%)

Reference： [1]Patent: US2008/262063,2008,A1 .Location in patent: Page/Page column 28-29
[2]Patent: US2008/267911,2008,A1 .Location in patent: Page/Page column 36

24
[ 67-64-1 ]
[ 58442-17-4 ]
[ 1021910-66-6 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of the compound of Preparation 155 (1.0 g, 6.8 mmol) in acetone (4 ml), at 0 C., was added dropwise aqueous sodium hydroxide solution (4 ml) and the reaction mixture was allowed to warm to room temperature and stirred for 2 h. The mixture was adjusted to pH 7 by addition of concentrated hydrochloric acid and extracted with ethyl acetate. The combined extracts were dried (MgSO4) and concentrated in vacuo to give 4-(1H-benzimidazol-6-yl)but-3-en-2-one (1.3 g) which was used directly.

Reference： [1]Patent: US2008/103130,2008,A1 .Location in patent: Page/Page column 35

25
[ 1056249-32-1 ]
[ 58442-17-4 ]
C₂₂H₁₅N₅O [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 4344 - 4347

26
[ 24131-30-4 ]
[ 58442-17-4 ]
[ 1072121-67-5 ]
(E)-5-[2-(3,5-dimethoxyphenyl)-ethenyl]-1H-benzoimidazole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 512 - 522

27
[ 59-48-3 ]
[ 58442-17-4 ]
[ 1168720-90-8 ]

Yield	Reaction Conditions	Operation in experiment
10%	With piperidine; In ethanol; at 90℃; for 0.25h;	Indolin-2-one (80 mg, 0.60 mmol), lH-benzo[

Reference： [1]Patent: WO2009/79767,2009,A1 .Location in patent: Page/Page column 107

28
[ 109-01-3 ]
[ 58442-17-4 ]
[ 1254162-24-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium cyanoborohydride; acetic acid; In N,N-dimethyl-formamide; at 20℃;	Example 5 5-(4-Methyl-piperazin-1-ylmethyl)-benzoimidazole-1-carboxylic acid te/f-butyl ester (as a mixture with the 6-regioisomer)Step 1 : 1 H-Benzimidazole-5-carbaldehyde (0.50 g, 3.4 mmol), 1-methylpiperazine (0.42 ml_, 3.8 mmol) and sodium cyanoborohydride (0.16 mg, 3.8 mmol) in DMF:AcOH (1 0: 1 , 10 ml.) were stirred overnight at room temperature. The mixture was concentrated in vacuo and then diluted with water and THF (~1 :1 ).

Reference： [1]Patent: WO2010/125402,2010,A1 .Location in patent: Page/Page column 111

29
NaBH(AcO)3 [ No CAS ]
[ 459-59-6 ]
[ 58442-17-4 ]
[ 1342888-87-2 ]

Yield	Reaction Conditions	Operation in experiment
0.035 g (13%)		Example 94 N-((1H-Benzo[d]imidazol-5-yl)methyl)(4-fluorophenyl)-N-methylmethanamine The compound was synthesized starting from benzimidazol-5-carbaldehyde (146 mg; 1 mmol; 1 eq.), 4-fluoro-N-methylaniline (0.147 ml; 1 mmol; 1 eq.); NaBH(AcO)3 (318 mg; 1.5 mmol; 1.5 eq.) and AcOH (0.095 ml; 1.5 mmol; 1.5 eq.) as described above. Yield: 0.035 g (13%); MS m/z: 270.1 [M+H]+; 1H-NMR (400 MHz, DMSO d6): delta 2.05 (s, 3H); 3.47 (s, 2H); 3.57 (s, 2H); 7.11-7.16 (m, 3H); 7.35-7.36 (m, 2H); 7.44-7.56 (m, 2H); 8.14 (s, 1H); HPLC (METHOD [A]): rt 7.14 min (95.9%)

Reference： [1]Patent: US2011/262388,2011,A1

30
CHCl₃/MeOH [ No CAS ]
[ 100-46-9 ]
[ 58442-17-4 ]
[ 5918-89-8 ]

Yield	Reaction Conditions	Operation in experiment
0.045 g (19%)	With sodium tetrahydroborate; In methanol; water;	Example 2 (Alternative Procedure): N-Benzyl-1H-benzo[d]imidazol-5-amine Benzimidazol-5-carbaldehyde (146 mg; 1 mmol; 1 eq.) was dissolved in MeOH (10 ml). Benzylamine (0.109 ml; 1 mmol; 1 eq.) was added and the mixture was stirred overnight. NaBH4 (57 mg; 1.5 mmol; 1.5 eq.) was added and stirring was continued overnight. The reaction was quenched by addition of water and extracted with ethyl acetate (3*25 ml). The combined organic layers were dried over Na2SO4 and evaporated. The residue was purified by flashchromatography on silica using a CHCl3/MeOH gradient. Yield: 0.045 g (19%); MS m/z: 238.4 [M+H]+; 1H-NMR (400 MHz, DMSO d6): delta 3.65 (s, 2H); 3.74 (s, 2H); 7.10-7.20 (m, 2H); 7.25-7.32 (m, 4H); 7.40-7.55 (m, 2H); 8.11 (s, 1H); 12.28 (br s, 1H); HPLC (METHOD [A]): rt 4.98 min (95.0%)

Reference： [1]Patent: US2011/262388,2011,A1

31
NaBH(AcO)3 [ No CAS ]
[ 103-69-5 ]
[ 58442-17-4 ]
[ 1342888-84-9 ]

Yield	Reaction Conditions	Operation in experiment
0.040 g (16%)		Example 92 N-((1H-Benzo[d]imidazol-5-yl)methyl)-2-phenylethanamine The compound was synthesized starting from benzimidazol-5-carbaldehyde (146 mg; 1 mmol; 1 eq.), phenylethylamine (0.126 ml; 1 mmol; 1 eq.); NaBH(AcO)3 (318 mg; 1.5 mmol; 1.5 eq.) and AcOH (0.095 ml; 1.5 mmol; 1.5 eq.) as described above. Yield: 0.040 g (16%); MS m/z: 252.2 [M+H]+; 1H-NMR (400 MHz, DMSO d6): delta 3.30 (br s, 4H); 3.81 (s, 2H); 7.12-7.27 (m, 9H); 8.13-8.14 (m, 1H); 12.30 (br s, 1H); HPLC (METHOD [A]): rt doublepeak 6.77/6.60 min (93.7%)

Reference： [1]Patent: US2011/262388,2011,A1

32
NaBH(AcO)3 [ No CAS ]
[ 5961-59-1 ]
[ 58442-17-4 ]
N-((1H-Benzo[d]imidazol-5-yl)methyl)(4-methoxyphenyl)-N-methylmethanamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.030 g (11%)		Example 93 N-((1H-Benzo[d]imidazol-5-yl)methyl)(4-methoxyphenyl)-N-methylmethanamine The compound was synthesized starting from benzimidazol-5-carbaldehyde (146 mg; 1 mmol; 1 eq.), 4-methoxy-N-methylaniline (137 mg g; 1 mmol; 1 eq.); NaBH(AcO)3 (318 mg; 1.5 mmol; 1.5 eq.) and AcOH (0.095 ml; 1.5 mmol; 1.5 eq.) as described above. Yield: 0.030 g (11%); MS m/z: 268.3 [M+H]+; 1H-NMR (400 MHz, DMSO d6): delta 2.89 (s, 3H); 3.64 (s, 3H); 4.53 (s, 2H); 6.71-6.78 (m, 4H); 7.05-7.07 (m, 1H); 7.35 (br s, 1H); 7.49 (d, 1H, 3J=8.3 Hz); 8.13 (s, 1H); 12.35 (br s, 1H); HPLC (METHOD [A]): rt 6.28 min (90.3%)

Reference： [1]Patent: US2011/262388,2011,A1

33
NaBH(AcO)3 [ No CAS ]
[ 58442-17-4 ]
[ 1342888-82-7 ]

Yield	Reaction Conditions	Operation in experiment
0.160 g (71%)	With aniline;	Example 91 N-((1H-Benzo[d]imidazol-5-yl)methyl)benzenamine The compound was synthesized starting from benzimidazol-5-carbaldehyde (146 mg; 1 mmol; 1 eq.), aniline (0.095 ml; 1 mmol; 1 eq.), NaBH(AcO)3 (318 mg; 1.5 mmol; 1.5 eq.) and AcOH (0.095 ml; 1.5 mmol; 1.5 eq.) as described above. Yield: 0.160 g (71%); MS m/z: 224.3 [M+H]+; 1H-NMR (400 MHz, DMSO d6): delta 4.34-4.35 (m, 2H); 6.20.6.21 (m, 1H); 6.45-6.49 (m, 1H); 6.57-6.59 (m, 1H); 6.98-7.02 (m, 1H); 7.17-7.26 (m, 2H); 7.39-7.43 (m, 1H); 7.49-7.52 (m, 2H); 12.34-12.39 (br m, 1H); HPLC (METHOD [A]): rt 8.16 min (97.3%)

Reference： [1]Patent: US2011/262388,2011,A1

34
[ 3260-49-9 ]
[ 58442-17-4 ]
[ 1613044-91-9 ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium hydroxide; In ethanol; water;Reflux;	General procedure: To a solution of 3 in ethanol (3mL/mmol) were added an aqueous solution of potassium hydroxide (50%, 5mL/mmol) and a benzaldehyde derivative (1.0-3.5equiv.). The solution was refluxed until TLC showed complete disappearance of the starting material (2-5h). After cooling, ethanol was removed under reduced pressure, then the residue was diluted into distilled water (50mL/mmol) and an aqueous solution of hydrochloric acid (10%) was added to adjust the pH to 2-3. The mixture was then extracted with ethyl acetate or dichloromethane. The combined organic layers were washed with water and brine, dried over MgSO4, filtered off and concentrated under reduced pressure to afford the corresponding crude (Z)-2-benzylidenebenzofuran-3(2H)-one derivative.

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 80,p. 579 - 592

35
2,4-dimethylcarbonohydrazide bis-hydrochloride [ No CAS ]
[ 58442-17-4 ]
C₁₁H₁₄N₆O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	In methanol; for 48h;Reflux;	A solution of <strong>[58442-17-4]5-formylbenzimidazole</strong> (0.25 g, 1.71 mmol) in5.5 mL of methanol was added dropwise to a solution of 2,4-dimethylcarbonohydrazidebis-hydrochloride (0.20 g, 1.71 mmol) in11 mL of hot methanol. This mixture was heated at reflux for48 h. Then, the reaction mixture was filtered and the solvent evaporatedunder reduced pressure. The solid residue was washed withethyl acetate and air-dried to give the BIm6mVH3 as a yellow solid(0.19 g, 45%).

Reference： [1]Polyhedron,2014,vol. 76,p. 36 - 44

36
carbonic acid bis(1-isopropylhydrazide) dihydrochloride [ No CAS ]
[ 58442-17-4 ]
1,5-diisopropyl-3-(benzimidazol-6-yl)-6-oxoverdazyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate; In ethanol; at 20℃; for 24h;	2,4-Diisopropylcarbonohydrazide bis-hydrochloride (70.0 mg,0.286 mmol) and <strong>[58442-17-4]5-formylbenzimidazole</strong> (41 mg, 0.286 mmol)were dissolved in a minimum amount of 95% ethanol. To this solutionwas added sodium acetate (47.0 mg, 0.572 mmol) in ethanoland the solution was stirred at room temperature for 24 h. Next,the mixture was filtered and the solution evaporated to give crudeproduct BIm6iVH3, which was dissolved in minimum amount ofdichloromethane and treated dropwise with a 0.25 M aqueoussolution of NaIO4 under argon gas with vigorous stirring, until anorange-red color was acquired. The reaction mixture was stirredfor 10 min and extracted multiple times with dichloromethane.The combined organic layers were dried over anhydrous MgSO4and evaporated to dryness under vacuo. The crude product waspurified by chromatography (silica, 2:3ethyl acetate:hexanes) togive BIm6iV, which was recrystallized from acetonitrile to giveorange-red, plate shaped crystals (46 mg, 54%, mp 188-191 C).ESR (toluene, 9.49 GHz): 6.60 G (2N), 5.17 (2N), 1.22 (2H). MS(EI+): calcd for C15H19N6O m/z = 299.1620, found m/z = 299.1622.

Reference： [1]Polyhedron,2014,vol. 76,p. 36 - 44

37
[ 14538-51-3 ]
[ 58442-17-4 ]
[ 1611492-22-8 ]

Yield	Reaction Conditions	Operation in experiment
28%	With triethylamine; In methanol; at 20℃; for 144h;Reflux;	2.3 2-(5'-Benzimidazole)-4,4,5,5-tetramethyl-4,5-dihydro-1,3-dihydroxy-1H-imidazole (BIm5NNH3) To a suspension of 2,3-bis(hydroxylamino)-2,3-dimethylbutane hydrogensulfate (0.675 g, 2.74 mmol) in 50 ml of absolute methanol (purged with argon) was added triethylamine (1.53 mL, 11.0 mmol). When the salt dissolved, <strong>[58442-17-4]5-formylbenzimidazole</strong> (0.400 g, 2.74 mmol) was added and the reaction stirred at room temperature for 6 days. The solvents were removed under reduced pressure to give a gummy white paste. Ethyl acetate was added, the slurry triturated, and the nitronylnitroxide precursor BIm5NNH3 was collected by vacuum filtration as a white solid (0.214 g, 28%, mp 224-226 C).

Reference： [1]Polyhedron,2014,vol. 76,p. 36 - 44

38
[ 24424-99-5 ]
[ 58442-17-4 ]
tert-butyl 5-formyl-1H-benzo[d]imidazole-1-carboxylate [ No CAS ]
tert-butyl 6-formyl-1H-benzo[d]imidazole-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; In dichloromethane; at 25℃; for 0.5h;	A solution of <strong>[58442-17-4]1H-benzo[d]imidazole-5-carbaldehyde</strong> (LXXII) (787 mg, 4.92 mmol, 1 eq) in DCM (5 mL) was added Boc2O (1.13 g, 5.2 mmol, 1.05 eq) and DMAP (60 mg, 0.492 mmol, 0.1 eq). The mixture was then stirred at 25 C. for 30 minutes before being poured into water (100 mL) and extracted with EtOAc (3×100 mL), the organic phases were combined, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a mixture of tert-butyl 5-formyl-1H-benzo[d]imidazole-1-carboxylate (LXXIII) and tert-butyl 6-formyl-1H-benzo[d]imidazole-1-carboxylate (LXXIV) as a white solid. (850 mg, 63.5%)1H NMR (CDCl3, 400 MHz) delta ppm 1.73 (s, 9H), 7.93 (s, 1H), 7.98 (dd, J=8.4 Hz, J=1.2 Hz, 1H), 8.16 (d, J=8.4 Hz, 1H), 8.30 (s, 1H), 8.55 (s, 1H), 8.60 (s, 1H), 10.12 (s, 1H); ESIMS found C13H14N2O3 m/z 247.1 (M+H)

Reference： [1]Patent: US2014/243349,2014,A1 .Location in patent: Paragraph 1755; 1756

39
[ 473895-86-2 ]
[ 58442-17-4 ]

Reference： [1]Patent: US2014/309427,2014,A1

40
(1⁽³⁾H-benzimidazol-5-yl)-acetic acid ethyl ester [ No CAS ]
[ 58442-17-4 ]

Reference： [1]Patent: US2014/309427,2014,A1

41
[ 32871-88-8 ]
[ 58442-17-4 ]
4-((1H-benzo[d]imidazol-5-yl)methyl)-6,7-dimethoxyisoquinoline dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With hydrogenchloride; In ethanol; water; at 90℃; for 0.5h;	General procedure: General Procedure A for Preparation of Compounds 1-20, 22, 25, 26, 28-31, 33, 34, 36-40, 43-45, 47-54, 57-72, 74, 78-83, 95, 102-105, 109, 110, 117, 119, 123, 124, 131, 132, 137, 143, 155, 161-163, 168, 169 and compounds SSA 48042, LPO 55070B, ANP 491748, ANP 53134 and ANP 53006AA solution of 37% aqueous HCl was added to a mixture of the corresponding aromatic aldehyde (or masked aldehyde) and aminoacetaldehyde diethyl acetal (in absolute EtOH (see conditions in tables 3 and 7). The reaction mixture was stirred in an ace pressure tube (Aldrich) according to the conditions described in tables 3 and 7. The reaction mixture was immediately cooled at 4 C. and concentrated to dryness under reduced pressure. EtOAc (typically 200 mL) was added to the residue and this mixture was poured into a 1 M aqueous K2CO3 solution (typically 50 mL). The separated organic layer was washed with brine (typically 20 mL), dried over MgSO4, filtered and evaporated to give a residue. This residue was purified by column chromatography (SiO2, see exact conditions in tables 3 and 7). After evaporation, if the hydrochloride salt was needed, the obtained free base (1 eq.) was dissolved in MeOH (2 mL) and a 1.75 N HCl solution in MeOH (2.1 eq.×number of basic nitrogen) was added (see conditions in tables 3 and 7). The desired isoquinoline, either as a free base or a hydrochloride salt, was obtained after further drying under vacuum.

Reference： [1]Patent: US2015/158895,2015,A1 .Location in patent: Paragraph 380; 381

42
2-(2-aminoethyl)-N-[(3-fluoropyridin-2-yl)methyl]-1,3-thiazole-4-carboxamide dihydrochloride [ No CAS ]
[ 58442-17-4 ]
2-{2-[(1H-1,3-benzodiazol-5-ylmethyl)amino]ethyl}-N-[(3-fluoropyridin-2-yl)methyl]-1,3-thiazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
207 mg		General procedure: A suspension of methyl 2-(2-aminoethyl)-1 ,3-thiazole-4-carboxylate (5) (1.96 g, 10.52 mmol), 1 H- benzimidazole-2-carbaldehyde (2.31 g, 15.79 mmol) and DIPEA (1.83 ml, 10.52 mmol) in MeOH (100 ml) was stirred at room temperature for 12 h. The reaction mixture was cooled to 0C, NaBH4 (0.597 g, 15.79 mmol) was added and the mixture stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and the residue dissolved in EtOAc (100 ml) and washed with saturated NC03 (2 x 50 ml). The combined aqueous layers were extracted with EtOAc (3 x 50 ml) and the combined organic layers dried (MgS04), filtered and evaporated in vacuo. Purification by flash column chromatography (KP- NH, eluting with a gradient of 0-10% MeOH / DCM) afforded the title compound (1.4 g, 38%, 90% purity) as a tan solid. 1 H-NMR (Methanol-d4, 250 MHz): d[ppm]= 8.27 (s, 1 H), 7.60 - 7.49 (m, 2H), 7.29 - 7.17 (m, 2H), 4.09 (s, 2H), 3.92 (s, 3H), 3.26 (t, J = 6.3 Hz, 2H), 3.10 (t, J = 6.8 Hz, 2H) HPLCMS (Method A): [m/z]: 317 [M+H]+In a similar fashion to general procedure 3, 2-(2-aminoethyl)-N-[(3-fluoropyridin-2-yl)methyl]-1 ,3-thiazole-4- carboxamide dihydrochloride (103) (400 mg, 0.64 mmol, 56% purity), 1 H-1 ,3-benzodiazole-5-carbaldehyde (1 12 mg , 0.77 mmol) and DIPEA (0.56 ml, 3.19 mmol) in MeOH (10 ml) at room temperature for 18 h, followed by by the addition of NaBH4 (36 mg , 0.96 mmol) gave the title compound (207 mg , 75.9%) as a cream solid following purification by flash column chromatography (KP-NH , eluting with a gradient of 0- 20% MeOH / DCM). 1H-NMR (Methanol-d4, 500 MHz): d[ppm]= 8.31 - 8.29 (m, 1H), 8.14 (s, 1H), 8.10 (s, 1H), 7.64 - 7.53 (m, 3H), 7.37-7.33 (m, 1H), 7.29 (dd, J = 8.3, 1.3 Hz, 1H), 4.79 (d, J = 1.6 Hz, 2H), 3.96 (s, 2H), 3.28 (t, J = 6.9 Hz, 2H), 3.09 (t, J = 6.9 Hz, 2H) HPLCMS (Method C): [m/z]: 411.2 [M+H]+

Reference： [1]Patent: WO2017/68089,2017,A2 .Location in patent: Page/Page column 137; 200; 201

43
[ 3218-49-3 ]
[ 58442-17-4 ]
(Z)-3-(1H-benzo[d]imidazol-6-yl)-2-(3,4-dichlorophenyl)acrylonitrile [ No CAS ]

Reference： [1]ChemMedChem,2018,vol. 13,p. 1447 - 1458

44
[ 58442-17-4 ]
[ 74-88-4 ]
[ 181867-19-6 ]
[ 279226-70-9 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: 4.94g (56.7mmol) of MnO2 were added to a solution of 1.40g (9.45mmol) of 7 in 50mL of MeOH. After 48hat rt, the mixture was filtered over slica and by evaporation 1.24g (90%) of compound 8 was isolated.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 158,p. 167 - 183

45
[ 95-54-5 ]
[ 58442-17-4 ]
[ 41292-72-2 ]

Reference： [1]New Journal of Chemistry,2018,vol. 42,p. 17931 - 17938

46
[ 5305-59-9 ]
[ 58442-17-4 ]
C₁₂H₉N₅O [ No CAS ]

Reference： [1]ACS Chemical Neuroscience,2019,vol. 10,p. 482 - 496

47
[ 58442-17-4 ]
C₁₅H₁₄N₆OS [ No CAS ]

Reference： [1]ACS Chemical Neuroscience,2019,vol. 10,p. 482 - 496

48
[ 58442-17-4 ]
1-ethyl-3-(6-(5-((prop-2-yn-1-ylamino)methyl)-1H-benzo[d]-imidazol-1-yl)pyrimidin-4-yl)thiourea [ No CAS ]

Reference： [1]ACS Chemical Neuroscience,2019,vol. 10,p. 482 - 496

49
[ 58442-17-4 ]
1-ethyl-3-(6-(5-((methyl(prop-2-yn-1-yl)amino)methyl)-1H-benzo[d]imidazol-1-yl)pyrimidin-4-yl)thiourea [ No CAS ]

Reference： [1]ACS Chemical Neuroscience,2019,vol. 10,p. 482 - 496

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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
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H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
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H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
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H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
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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
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Health hazards
Code	Phrase
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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. 58442-17-4 ]

Quality Control of [ 58442-17-4 ]

Related Doc. of [ 58442-17-4 ]

Product Details of [ 58442-17-4 ]

Calculated chemistry of [ 58442-17-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 58442-17-4 ]

Application In Synthesis of [ 58442-17-4 ]

[ 58442-17-4 ] Synthesis Path-Upstream 1~2

[ 58442-17-4 ] Synthesis Path-Downstream 1~49

Related Functional Groups of [ 58442-17-4 ]

Aldehydes

Related Parent Nucleus of [ 58442-17-4 ]

Benzimidazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 58442-17-4 ]

Related Parent Nucleus of
[ 58442-17-4 ]