[ CAS No. 1265229-25-1 ] {[proInfo.proName]}

Name: 1265229-25-1|(5-Amino-1-(2-methyl-1H-benzo[d]imidazol-6-yl)-1H-pyrazol-4-yl)(1H-indol-2-yl)methanone|98%
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Quality Control of [ 1265229-25-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1265229-25-1 ]

SDS Specification

Alternatived Products of [ 1265229-25-1 ]

Product Details of [ 1265229-25-1 ]

CAS No. :	1265229-25-1	MDL No. :	MFCD28502053
Formula :	C₂₀H₁₆N₆O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BEMNJULZEQTDJY-UHFFFAOYSA-N
M.W :	356.38	Pubchem ID :	66555680
Synonyms :	Debio 1347;CH5183284;FF284	Chemical Name :	(5-Amino-1-(2-methyl-1H-benzo[d]imidazol-6-yl)-1H-pyrazol-4-yl)(1H-indol-2-yl)methanone

Calculated chemistry of [ 1265229-25-1 ]

Physicochemical Properties

Num. heavy atoms :	27
Num. arom. heavy atoms :	23
Fraction Csp3 :	0.05
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	3.0
Molar Refractivity :	104.32
TPSA :	105.38 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.73 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.86
Log Po/w (XLOGP3) :	3.86
Log Po/w (WLOGP) :	3.36
Log Po/w (MLOGP) :	1.7
Log Po/w (SILICOS-IT) :	3.18
Consensus Log Po/w :	2.79

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.91
Solubility :	0.00435 mg/ml ; 0.0000122 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.77
Solubility :	0.000606 mg/ml ; 0.0000017 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-6.78
Solubility :	0.0000596 mg/ml ; 0.000000167 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.78

Safety of [ 1265229-25-1 ]

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 [ 1265229-25-1 ]

* 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 [ 1265229-25-1 ]
Downstream synthetic route of [ 1265229-25-1 ]

[ 1265229-25-1 ] Synthesis Path-Upstream 1~4

1
[ 1265231-79-5 ]
[ 1265229-25-1 ]

Yield	Reaction Conditions	Operation in experiment
63%	With water; sodium hydroxide In ethanol at 20℃; for 2 h;	[Example 1: Synthesis of [5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(1H-indol-2-yl)-methanone] An aqueous solution (1.67 ml) of 4 M sodium hydroxide was added to an ethanol solution (17 ml) of [5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(1-benzenesulfonyl-1H-indol-2-yl) methanone (87 mg). The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into water. The resulting solid was collected by filtration, washed with water, and dried to give [5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(1H-indol-2-yl) methanone (40 mg, 63percent). ¹H-NMR (DMSO-D₆) δ: 12.47 (1H, s), 11.70 (1H, s), 8.32 (1H, s), 7.70 (1H, d, J = 8.0 Hz), 7.66-7.55 (2H, m), 7.50-7.45 (2H, m), 7.31-7.23 (2H, m), 7.10-7.06 (1H, m), 7.01 (2H, brs), 2.53 (3H, s) ESI (LC-MS positive mode) m/z 357 [(M+H)⁺]

Reference： [1] Patent: EP2471786, 2012, A1, . Location in patent: Page/Page column 56

2
[ 1265231-91-1 ]
[ 1265229-25-1 ]

Reference： [1] Patent: EP2471786, 2012, A1,

3
[ 1265234-00-1 ]
[ 1265229-25-1 ]

Reference： [1] Patent: EP2471786, 2012, A1,

4
[ 40899-92-1 ]
[ 1265229-25-1 ]

Reference： [1] Patent: EP2471786, 2012, A1,

[ 1265229-25-1 ] Synthesis Path-Downstream 1~7

1
[ 1265231-79-5 ]
[ 1265229-25-1 ]

Yield	Reaction Conditions	Operation in experiment
63%	With water; sodium hydroxide; In ethanol; at 20.0℃; for 2.0h;	[Example 1: Synthesis of [5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(1H-indol-2-yl)-methanone] An aqueous solution (1.67 ml) of 4 M sodium hydroxide was added to an ethanol solution (17 ml) of [5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(1-benzenesulfonyl-1H-indol-2-yl) methanone (87 mg). The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into water. The resulting solid was collected by filtration, washed with water, and dried to give [5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(1H-indol-2-yl) methanone (40 mg, 63%). 1H-NMR (DMSO-D6) delta: 12.47 (1H, s), 11.70 (1H, s), 8.32 (1H, s), 7.70 (1H, d, J = 8.0 Hz), 7.66-7.55 (2H, m), 7.50-7.45 (2H, m), 7.31-7.23 (2H, m), 7.10-7.06 (1H, m), 7.01 (2H, brs), 2.53 (3H, s) ESI (LC-MS positive mode) m/z 357 [(M+H)+]

Reference： [1]Patent: EP2471786,2012,A1 .Location in patent: Page/Page column 56

2
[ 1265231-91-1 ]
[ 1265229-25-1 ]

Reference： [1]Patent: EP2471786,2012,A1

3
[ 97-67-6 ]
[ 1265229-25-1 ]
[5-amino-1-(2-methyl-3H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(1H-indol-2-yl)-methanone L-malate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	In dimethyl sulfoxide; acetone;	[Example 1A] Synthesis of [5-amino-1-(2-methyl-3H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(1H-indol-2-yl)-methanone L-malate Predetermined amounts of L-malic acid (68 g, 0.507 mol) and [5-amino-1-(2-methyl-3H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(1H-indol-2-yl)-methanone hydrate (190 g, 0.507 mol) were dissolved in dimethyl sulfoxide (0.418 1, 2.2 v/w) and acetone (0.4181, 2.2 v/w). Then, the resulting solution was filtered using a Kiriyama rohto (No. 4 paper filter), and placed into a 10-1 separable flask with a jacket. The reaction solution was heated at 50C for dissolution. A predetermined amount of L-malic acid (544.4 g, 4.06 mol) was dissolved in acetone (1.25 1, 6.6 v/w) and acetic acid (0.418 1, 2.2 v/w). Then, the resulting solution was filtered using a Kiriyama rohto (No. 4 paper filter), and placed into a 10-1 separable flask with a jacket while keeping the inner temperature at 45C or higher. The seed crystal (0.95 g, 0.5%) was suspended in acetone (7.5 ml), and then this was placed into a 10-1 separable flask with a jacket. After seven hours, the suspension was cooled to 25C. The crystals were collected by filtration using a Kiriyama rohto, and washed twice with acetone (0.851, 5 v/w). The resulting wet powder was placed into a 10-1 separable flask with a jacket. Acetone (2.85 1, 15 v/w) was added into the flask, and the suspension was stirred for three hours at 50C. The resulting crystals were collected by filtration using a Kiriyama rohto, and washed twice with acetone (0.851, 5 v/w). The resulting wet powder was dried for three hours under reduced pressure at an outer temperature of 40C to provide [5-amino-1-(2-methyl-3H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(1H-indol-2-yl)-methanone L-malate (556.9 g, 73%). 1H-NNM (DMSO-D6) delta: 11.69 (1H, s), 8.31 (1H, s), 8.25-7.00 (10H, m), 4.25-4.22 (1H, m), 3.33 (2H, brs), 2.69-2.32 (9H, m) FAB positive mode m/z 157.1, 232.1, 289.2, 357.2 [(M+H)+]

Reference： [1]Patent: EP2471786,2012,A1 .Location in patent: Page/Page column 56-57

4
[ 75-75-2 ]
[ 1265229-25-1 ]
[5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(1H-indol-2-yl)-methanone methanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	In water; N,N-dimethyl-formamide; at 20.0℃; for 0.333333h;	[Example 1C] Synthesis of <strong>[1265229-25-1][5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(1H-indol-2-yl)-methanone</strong> 1-methanesulfonate monohydrate An aqueous solution (64.9 ml) of 2 M methanesulfonic acid was added to a dimethylformamide solution (420 ml) of <strong>[1265229-25-1][5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(1H-indol-2-yl)-methanone</strong> (42 g). This was stirred at room temperature for 20 minutes. Then, methyl-t-butyl ether (105 ml) was added to the reaction solution. 3.0 mg of a seed crystal was added thereto, and this was stirred at room temperature. After confirmation of crystal precipitation, methyl-t-butyl ether (105 ml) was divided into four portions and separately added to the reaction solution at 15-minute intervals. The reaction solution was stirred at room temperature for 1.5 hours. The resulting crystals were collected by filtration using a Kiriyama rohto. The solid collected by filtration was washed three times with methyl-t-butyl ether (210 ml), and dried to provide <strong>[1265229-25-1][5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(1H-indol-2-yl)-methanone</strong> 1-methanesulfonate monohydrate (42.68 g, 84%). 1H-NMR (DMSO-D6) delta: 11.70 (1H, s), 8.39 (1H, s), 7.99 (1H, d, J = 1.6 Hz), 7.94 (1H, d, J = 8.8 Hz), 7.74-7.68 (2H, m), 7.51-7.46 (2H, m), 7.29-7.18 (3H, m), 7.11-7.06 (1H, m), 2.84 (3H, s), 2.37 (3H, s) ESI (LC-MS positive mode) m/z 357 [(M+H)+]

Reference： [1]Patent: EP2471786,2012,A1 .Location in patent: Page/Page column 58

5
[ 1265229-25-1 ]
[5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(1H-indol-2-yl)-methanone hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With hydrogenchloride; In water; N,N-dimethyl-formamide; at 25.0℃;	[Example 1B] Synthesis of <strong>[1265229-25-1][5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(1H-indol-2-yl)-methanone</strong> hydrochloride [5-Amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(1H-indol-2-yl)-metha none (194 mg) was dissolved in dimethylformamide (1.94 ml). An aqueous solution of 2 M hydrochloric acid (300 mul) was divided into five portions and separately added dropwise thereto at 25C. 2-Propanol (4 ml) was divided into three portions and separately added to the reaction solution at five-minute intervals. The resulting precipitate was collected by filtration, and washed with 2-propanol (1 ml). Then, the powder was dried under reduced pressure at 40C. This yielded an opalescent powder (188 mg, 88%). 11.72 (1H, s), 8.39 (1H, s), 7.96 (1H, d, J = 2.1 Hz), 7.92 (1H, d, J = 8.7 Hz), 7.71 (1H, t, J = 2.1 Hz), 7.68 (1H, t, J = 2.1 Hz), 7.51 (1H, s), 7.48 (1H, d, J = 2.1 Hz), 7.28 (1H, d, J = 7.6 Hz), 7.23 (3H, s), 7.09 (1H, t, J = 7.6 Hz), 2.82 (3H, s). ESI (LC-MS positive mode) m/z 357 [(M+H)+]

Reference： [1]Patent: EP2471786,2012,A1 .Location in patent: Page/Page column 57

6
[ 1265234-00-1 ]
[ 1265229-25-1 ]

Reference： [1]Patent: EP2471786,2012,A1

7
[ 40899-92-1 ]
[ 1265229-25-1 ]

Reference： [1]Patent: EP2471786,2012,A1

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H200	Unstable explosive
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H250	Catches fire spontaneously if exposed to air
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H260	In contact with water releases flammable gases which may ignite spontaneously
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H316	Causes mild skin irritation
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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. 1265229-25-1 ] {[proInfo.proName]}

Quality Control of [ 1265229-25-1 ]

Related Doc. of [ 1265229-25-1 ]

Product Details of [ 1265229-25-1 ]

Calculated chemistry of [ 1265229-25-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1265229-25-1 ]

Application In Synthesis of [ 1265229-25-1 ]

[ 1265229-25-1 ] Synthesis Path-Upstream 1~4

[ 1265229-25-1 ] Synthesis Path-Downstream 1~7

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry