[ CAS No. 177476-76-5 ] {[proInfo.proName]}

Name: 177476-76-5|4-Amino-3-methoxybenzonitrile|98%
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SKU: A105986
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Quality Control of [ 177476-76-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 177476-76-5 ]

SDS Specification

Alternatived Products of [ 177476-76-5 ]

Product Details of [ 177476-76-5 ]

CAS No. :	177476-76-5	MDL No. :	MFCD13250177
Formula :	C₈H₈N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SCXGWOFGMVEUGW-UHFFFAOYSA-N
M.W :	148.16	Pubchem ID :	11815931
Synonyms :

Calculated chemistry of [ 177476-76-5 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	42.05
TPSA :	59.04 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 :	Yes
Log Kp (skin permeation) :	-6.53 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.53
Log Po/w (XLOGP3) :	0.95
Log Po/w (WLOGP) :	1.16
Log Po/w (MLOGP) :	0.51
Log Po/w (SILICOS-IT) :	1.07
Consensus Log Po/w :	1.04

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.69
Solubility :	2.99 mg/ml ; 0.0202 mol/l
Class :	Very soluble
Log S (Ali) :	-1.78
Solubility :	2.48 mg/ml ; 0.0167 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.23
Solubility :	0.868 mg/ml ; 0.00586 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.38

Safety of [ 177476-76-5 ]

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

Application In Synthesis of [ 177476-76-5 ]

* 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 [ 177476-76-5 ]
Downstream synthetic route of [ 177476-76-5 ]

[ 177476-76-5 ] Synthesis Path-Upstream 1~6

1
[ 177476-75-4 ]
[ 177476-76-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogen In ethyl acetate at 20℃; for 0.75 h;	To the suspension of 3-methoxy-4-nitrobenzonitrile (11.4 g, 64 mmol) in ethyl acetate (60 mL) was added 10percent Pd/C (1 g). The reaction mixture was vigorously shaken in a Parr under an atmosphere of hydrogen (50 psi) at room temperature for 45 min. The mixture was filtered through a short pad of celite, and the filtrate was concentrated to give 4-amino-3-methoxy-benzonitrile as a yellow oil, which solidified at stand (9.5 g, 95percent)
95%	With hydrogen In ethyl acetate at 20℃; for 0.75 h;	Step c: To the suspension of 3-methoxy-4-nitrobenzonitrile (11.4 g, 64 mmol) in ethyl acetate (60 mL) was added 10percent Pd/C (1 g). The reaction mixture was vigorously shaken in a Parr under an atmosphere of hydrogen (50 psi) at room temperature for 45 min. The mixture was filtered through a short pad of celite, and the filtrate was concentrated to give 4-amino-3-methoxy-benzonitrile as a yellow oil, which solidified at stand (9.5 g, 95percent)
95%	With hydrogen In ethyl acetate at 20℃; for 0.75 h;	Step c: To the suspension of 3-methoxy-4-nitrobenzonitrile (11.4 g, 64 mmol) in ethyl acetate (60 mL) was added 10percent Pd/C (1 g). The reaction mixture was vigorously shaken in a Parr under an atmosphere of hydrogen (50 psi) at room temperature for 45 min. The mixture was filtered through a short pad of celite, and the filtrate was concentrated to give 4-amino-3-methoxy-benzonitrile as a yellow oil, which solidified at stand (9.5 g, 95percent)

Reference： [1] Patent: US2011/130398, 2011, A1, . Location in patent: Page/Page column 34
[2] Patent: US2011/269809, 2011, A1, . Location in patent: Page/Page column 13
[3] Patent: US2012/46306, 2012, A1, . Location in patent: Page/Page column 33
[4] Journal of Medicinal Chemistry, 2000, vol. 43, # 6, p. 1187 - 1202
[5] Patent: US5506252, 1996, A,

2
[ 1527-89-5 ]
[ 177476-76-5 ]

Reference： [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 6, p. 1187 - 1202

3
[ 5081-36-7 ]
[ 177476-76-5 ]

Reference： [1] Patent: US2011/130398, 2011, A1,
[2] Patent: US2011/269809, 2011, A1,
[3] Patent: US2012/46306, 2012, A1,

4
[ 92241-87-7 ]
[ 177476-76-5 ]

Reference： [1] Patent: US2011/130398, 2011, A1,
[2] Patent: US2011/269809, 2011, A1,

5
[ 59557-91-4 ]
[ 177476-76-5 ]

Reference： [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 1, p. 254 - 272

6
[ 67579-92-4 ]
[ 177476-76-5 ]

Reference： [1] Patent: US2011/130398, 2011, A1,

[ 177476-76-5 ] Synthesis Path-Downstream 1~59

1
[ 5231-87-8 ]
[ 177476-76-5 ]
[ 177476-72-1 ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 1187 - 1202

2
[ 177476-75-4 ]
[ 177476-76-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogen;palladium 10% on activated carbon; In ethyl acetate; at 20℃; under 2585.81 Torr; for 0.75h;	To the suspension of 3-methoxy-4-nitrobenzonitrile (11.4 g, 64 mmol) in ethyl acetate (60 mL) was added 10% Pd/C (1 g). The reaction mixture was vigorously shaken in a Parr under an atmosphere of hydrogen (50 psi) at room temperature for 45 min. The mixture was filtered through a short pad of celite, and the filtrate was concentrated to give 4-amino-3-methoxy-benzonitrile as a yellow oil, which solidified at stand (9.5 g, 95%)
95%	With hydrogen;palladium 10% on activated carbon; In ethyl acetate; at 20℃; under 2585.81 Torr; for 0.75h;	Step c: To the suspension of 3-methoxy-4-nitrobenzonitrile (11.4 g, 64 mmol) in ethyl acetate (60 mL) was added 10% Pd/C (1 g). The reaction mixture was vigorously shaken in a Parr under an atmosphere of hydrogen (50 psi) at room temperature for 45 min. The mixture was filtered through a short pad of celite, and the filtrate was concentrated to give 4-amino-3-methoxy-benzonitrile as a yellow oil, which solidified at stand (9.5 g, 95%)
95%	With hydrogen;palladium 10% on activated carbon; In ethyl acetate; at 20℃; under 2585.81 Torr; for 0.75h;	Step c: To the suspension of 3-methoxy-4-nitrobenzonitrile (11.4 g, 64 mmol) in ethyl acetate (60 mL) was added 10% Pd/C (1 g). The reaction mixture was vigorously shaken in a Parr under an atmosphere of hydrogen (50 psi) at room temperature for 45 min. The mixture was filtered through a short pad of celite, and the filtrate was concentrated to give 4-amino-3-methoxy-benzonitrile as a yellow oil, which solidified at stand (9.5 g, 95%)

1.3 g (60%)

platinum; In ethanol;

3-Methoxy-4-nitrobenzonitrile (2.6 g, 14.6 mmol) was suspended in ethanol(100 mL) and added to a mixture of 5% platinum on carbon (250 mg) in ethanol (150 mL). The reaction mixture was stirred under a hydrogen gas atmosphere. After 24 h the reaction was filtered, concentrated, and chromatographed (ethyl acetate/hexanes, 25/75) to yield 1.3 g (60%) of 4-amino-3-methoxybenzonitrile: 1 H NMR (DMSO-d6): delta 7.1 (m, 2H), 6.65 (d, 1H), 5.77 (br s, 2H), 3.79 (s,

Reference： [1]Patent: US2011/130398,2011,A1 .Location in patent: Page/Page column 34
[2]Patent: US2011/269809,2011,A1 .Location in patent: Page/Page column 13
[3]Patent: US2012/46306,2012,A1 .Location in patent: Page/Page column 33
[4]Journal of Medicinal Chemistry,2000,vol. 43,p. 1187 - 1202
[5]Patent: US5506252,1996,A

3
[ 1527-89-5 ]
[ 177476-76-5 ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 1187 - 1202

4
[ 177476-76-5 ]
WAY-135201 [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 1187 - 1202

5
[ 177476-76-5 ]
[ 1098534-46-3 ]

Yield	Reaction Conditions	Operation in experiment
	With chlorosulfonic acid; In chloroform;	N-(4-cyano-2-methoxyphenyl)-sulfamic acid. To a solution of <strong>[177476-76-5]4-cyano-2-methoxyaniline</strong> (1 mmol) in chloroform (1 mL) at -78 C. is added chlorosulfonic acid. Upon reaction completion, the crude material is concentrated and may be purified by recrystalization to give N-(4-cyano-2-methoxyphenyl)-sulfamic acid.

Reference： [1]Patent: US2003/55260,2003,A1

6
[ 59557-91-4 ]
copper(l) cyanide [ No CAS ]
[ 177476-76-5 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 254 - 272

7
[ 177476-76-5 ]
[ 1201666-80-9 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 254 - 272

8
[ 5750-76-5 ]
[ 177476-76-5 ]
[ 1022968-95-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 463 - 466

9
[ 92241-87-7 ]
[ 177476-76-5 ]

Reference： [1]Patent: US2011/130398,2011,A1
[2]Patent: US2011/269809,2011,A1

10
[ 5081-36-7 ]
[ 177476-76-5 ]

Reference： [1]Patent: US2011/130398,2011,A1
[2]Patent: US2011/269809,2011,A1
[3]Patent: US2012/46306,2012,A1

11
[ 67579-92-4 ]
[ 177476-76-5 ]

Reference： [1]Patent: US2011/130398,2011,A1

12
[ 1303606-45-2 ]
[ 177476-76-5 ]
[ 1345866-82-1 ]

Yield	Reaction Conditions	Operation in experiment
		Example 16 Preparation of chiral(2'R,3'S,4'S,5'R)-6-Chloro-4'-(3-chloro-2-fluoro-phenyl)-2'-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid(4-carbamoyl-2-methoxy-phenyl)-amide; To a solution of chiral chiral(2'R,3'S,4'S,5'R)-6-chloro-4'-(3-chloro-2-fluoro-phenyl)-2'-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid (1 g, 2.1 mmol) in dichloromethane (20 mL) was added diisopropylethylamine (1 g, 7.7 mmol), diphenylphosphinic chloride (Aldrich) (1.2 g, 5.1 mmol) respectively. The mixture was stirred at room temperature for 8 min, then <strong>[177476-76-5]4-amino-3-methoxy-benzonitrile</strong> (0.56 g, 3.8 mmol) was added. The reaction mixture was stirred at room temperature for 66 h. The mixture was concentrated. The residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with water, brine, dried over Na2SO4, then concentrated. The residue was purified by chromatography (15% of EtOAc in CH2Cl2) to give crude chiral(2'R,3'S,4'S,5'R)-6-chloro-4'-(3-chloro-2-fluoro-phenyl)-2'-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid(4-cyano-2-methoxy-phenyl)-amide (0.14 g) which was used directly to the next step.

Reference： [1]Patent: US2011/269809,2011,A1 .Location in patent: Page/Page column 12

13
[ 4530-20-5 ]
[ 177476-76-5 ]
[ 1360822-02-1 ]