[ CAS No. 74420-00-1 ] {[proInfo.proName]}

Name: 74420-00-1|4-Amino-1H-pyrrolo[2,3-b]pyridine|97%
Brand: Ambeed
SKU: A218831
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Quality Control of [ 74420-00-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 74420-00-1 ]

Product Details of [ 74420-00-1 ]

CAS No. :	74420-00-1	MDL No. :	MFCD07778366
Formula :	C₇H₇N₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RCWISWVYKNLXHC-UHFFFAOYSA-N
M.W :	133.15	Pubchem ID :	639249
Synonyms :

Calculated chemistry of [ 74420-00-1 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	40.5
TPSA :	54.7 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) :	-6.66 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.95
Log Po/w (XLOGP3) :	0.63
Log Po/w (WLOGP) :	1.15
Log Po/w (MLOGP) :	0.37
Log Po/w (SILICOS-IT) :	1.36
Consensus Log Po/w :	0.89

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.73
Solubility :	2.49 mg/ml ; 0.0187 mol/l
Class :	Very soluble
Log S (Ali) :	-1.35
Solubility :	5.9 mg/ml ; 0.0443 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.52
Solubility :	0.404 mg/ml ; 0.00303 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 74420-00-1 ]

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 [ 74420-00-1 ]

* 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 [ 74420-00-1 ]
Downstream synthetic route of [ 74420-00-1 ]

[ 74420-00-1 ] Synthesis Path-Upstream 1~10

1
[ 74420-00-1 ]
[ 55052-28-3 ]

Reference： [1] Patent: WO2004/39796, 2004, A1, . Location in patent: Page/Page column 66

2
[ 74420-06-7 ]
[ 74420-00-1 ]

Reference： [1] Patent: WO2004/39796, 2004, A1, . Location in patent: Page/Page column 65
[2] Journal of Medicinal Chemistry, 1982, vol. 25, # 10, p. 1258 - 1261
[3] Journal of Organic Chemistry, 1980, vol. 45, # 20, p. 4045 - 4048
[4] Journal of Physical Chemistry A, 2003, vol. 107, # 10, p. 1459 - 1471
[5] Journal of Medicinal Chemistry, 1982, vol. 25, # 10, p. 1258 - 1261

3
[ 83683-82-3 ]
[ 74420-00-1 ]

Reference： [1] Journal of Medicinal Chemistry, 1982, vol. 25, # 10, p. 1258 - 1261

4
[ 361370-27-6 ]
[ 74420-00-1 ]

Reference： [1] Patent: WO2005/82367, 2005, A1, . Location in patent: Page/Page column 42

5
[ 640735-22-4 ]
[ 74420-00-1 ]

Reference： [1] Organic Letters, 2003, vol. 5, # 26, p. 5023 - 5025

6
[ 271-63-6 ]
[ 74420-00-1 ]

Reference： [1] Journal of Medicinal Chemistry, 1982, vol. 25, # 10, p. 1258 - 1261
[2] Journal of Medicinal Chemistry, 1982, vol. 25, # 10, p. 1258 - 1261
[3] Patent: WO2004/39796, 2004, A1,

7
[ 55052-24-9 ]
[ 74420-00-1 ]

Reference： [1] Journal of Medicinal Chemistry, 1982, vol. 25, # 10, p. 1258 - 1261
[2] Journal of Medicinal Chemistry, 1982, vol. 25, # 10, p. 1258 - 1261
[3] Patent: WO2004/39796, 2004, A1,

8
[ 55052-28-3 ]
[ 74420-00-1 ]

Reference： [1] Organic Letters, 2003, vol. 5, # 26, p. 5023 - 5025

9
[ 74420-00-1 ]
[ 74420-02-3 ]
[ 640735-23-5 ]

Reference： [1] Organic Letters, 2003, vol. 5, # 26, p. 5023 - 5025

10
[ 74420-00-1 ]
[ 74420-02-3 ]
[ 640735-23-5 ]

Reference： [1] Organic Letters, 2003, vol. 5, # 26, p. 5023 - 5025

[ 74420-00-1 ] Synthesis Path-Downstream 1~38

1
[ 109-65-9 ]
[ 74420-00-1 ]
1-Butyl-1H-pyrrolo[2,3-b]pyridin-4-ylamine [ No CAS ]
7-Butyl-7H-pyrrolo[2,3-b]pyridin-4-ylamine [ No CAS ]

Reference： [1]Tetrahedron,1993,vol. 49,p. 7337 - 7352

2
[ 3587-60-8 ]
[ 74420-00-1 ]
7-Benzyloxymethyl-7H-pyrrolo[2,3-b]pyridin-4-ylamine [ No CAS ]
1-Benzyloxymethyl-1H-pyrrolo[2,3-b]pyridin-4-ylamine [ No CAS ]

Reference： [1]Tetrahedron,1993,vol. 49,p. 7337 - 7352

3
[ 107-59-5 ]
[ 74420-00-1 ]
(4-Amino-pyrrolo[2,3-b]pyridin-1-yl)-acetic acid tert-butyl ester [ No CAS ]
(4-Amino-pyrrolo[2,3-b]pyridin-7-yl)-acetic acid tert-butyl ester [ No CAS ]

Reference： [1]Tetrahedron,1993,vol. 49,p. 7337 - 7352

4
[ 74420-06-7 ]
[ 74420-00-1 ]

Reference： [1]Patent: WO2004/39796,2004,A1 .Location in patent: Page/Page column 65
[2]Journal of Medicinal Chemistry,1982,vol. 25,p. 1258 - 1261
[3]Journal of Organic Chemistry,1980,vol. 45,p. 4045 - 4048
[4]Journal of Physical Chemistry A,2003,vol. 107,p. 1459 - 1471
[5]Journal of Medicinal Chemistry,1982,vol. 25,p. 1258 - 1261

5
[ 74420-00-1 ]
[ 100-44-7 ]
1-Benzyl-1H-pyrrolo[2,3-b]pyridin-4-ylamine [ No CAS ]
7-Benzyl-7H-pyrrolo[2,3-b]pyridin-4-ylamine [ No CAS ]

Reference： [1]Tetrahedron,1993,vol. 49,p. 7337 - 7352

6
[ 83683-82-3 ]
[ 74420-00-1 ]

Reference： [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 1258 - 1261

7
[ 74420-00-1 ]
[ 74420-02-3 ]
[ 640735-23-5 ]

Reference： [1]Organic Letters,2003,vol. 5,p. 5023 - 5025

8
[ 640735-22-4 ]
[ 74420-00-1 ]

Reference： [1]Organic Letters,2003,vol. 5,p. 5023 - 5025

9
[ 55052-28-3 ]
[ 74420-00-1 ]

Reference： [1]Organic Letters,2003,vol. 5,p. 5023 - 5025

10
[ 271-63-6 ]
[ 74420-00-1 ]

Reference： [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 1258 - 1261
[2]Journal of Medicinal Chemistry,1982,vol. 25,p. 1258 - 1261
[3]Patent: WO2004/39796,2004,A1

11
[ 55052-24-9 ]
[ 74420-00-1 ]

Reference： [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 1258 - 1261
[2]Journal of Medicinal Chemistry,1982,vol. 25,p. 1258 - 1261
[3]Patent: WO2004/39796,2004,A1

12
[ 173897-73-9 ]
[ 74420-00-1 ]
[ 173897-93-3 ]

Yield	Reaction Conditions	Operation in experiment
330 mg		Then, the crystals were dissolved in acetonitrile (10 mL) and added dropwise to a solution of <strong>[74420-00-1]4-amino-1H-pyrrolo[2,3-b]pyridine</strong> (240 mg) and diisopropylethylamine (520 mg) in acetonitrile (10 mL), and the mixture was stirred at room temperature for 8 hrs. The precipitated crystals were collected by filtration, dried and dissolved in methanol (7 mL). Sodium methoxide (60 mg) was added and the mixture was stirred at room temperature for 30 min. After the reaction, the mixture was concentrated under reduced pressure. Water was added to the obtained residue and the mixture was extracted with ethyl acetate. The extract was dried and the solvent was evaporated under reduced pressure. The obtained crystals were washed with ethyl acetate to give (R)-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-4-(1-benzyloxycarbonylaminoethyl)benzamide (330 mg). PMR (DMSO-d6/TMS) delta: 1.33-1.40 (3H, m), 4.72-4.78 (1H, m), 4.98-5.04 (2H, m), 6.78-6.82 (1H, m), 7.32-8.16 (13H, m)

Reference： [1]Patent: EP1195372,2002,A1 .Location in patent: Page 52-53
[2]Patent: EP1378247,2016,B1 .Location in patent: Paragraph 0076

13
[ 361370-27-6 ]
[ 74420-00-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; for 4h;	To a solution of 7-azaindole (5g, 42.3 mmol) in DCM (42 ml, 1M) cooled at 0C, was portionwise added 3-chloroperoxybenzoic acid (70-75%, 29.1 g, 4 eq). The reaction mixture was stirred for 1 hour. The reaction mixture was diluted with DCM (42 ml). The solid was removed by filtration. The 1H pyrrolo [2, 3-b] pyridine 7-oxide, was extracted with aqueous 1M HCl (3x200 ml). The aqueous layer was evaporated, yielding the 1H pyrrolo [2, 3-b] pyridine 7-oxide, as an orange powder, which was used without further purification. To the crude the 1H pyrrolo [2, 3-b] pyridine 7-oxide (5 g), was added POC13 (50 ml). The reaction mixture was stirred at 100C for 5 hours. The solution was cooled at 0C (with an ice-bath), and ice/water was carefully added (100 ml). An aqueous 6M NaOH was carefully added until pH=10. The precipitate was filtered off, washed with water and then dried, yielding the 4-chloro-lH-pyrrolo [2, 3-b] pyridine as a brown powder (77% yield starting from the 7-azaindole). To a solution of 4-chloro-1H-pyrrolo [2, 3-b] pyridine (4.45 g) in DMF (0.5 M) were added sodium azide (5 eq) and ammonium chloride (5 eq). The reaction mixture was heated at 110C for 5 hours. The solvent was evaporated, and water (200 ml) was added. The product was extracted with EtOAc (3x200 ml). The combined organic layers were evaporated. The residue was purified by flash chromatography (Cyclohexane/EtOAc 7/3, Ri0. 15), yielding the 4-azido-lH-pyrrolo [2, 3-b] pyridine as a beige powder (77% yield). The 4-azido-lH-pyrrolo [2, 3-b] pyridine (500 mg) was dissolved in EtOH, and Pd/C (10%) was added. The reaction mixture was stirred at RT for 4 hours, under H2 (3 atm). Pd/C was removed by filtration and then the filtrate was evaporated, pyridine a beige powder (100% yield).

Reference： [1]Patent: WO2005/82367,2005,A1 .Location in patent: Page/Page column 42

14
[ 74420-00-1 ]
[ 55052-28-3 ]

Reference： [1]Patent: WO2004/39796,2004,A1 .Location in patent: Page/Page column 66

15
trans-4-(1,3-dibenzyloxycarbonylguanidinomethyl)cyclohexanecarboxylic chloride [ No CAS ]
[ 74420-00-1 ]
trans-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-4-(1-benzyloxycarbonylguanidinomethyl)cyclohexanecarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate; N-ethyl-N,N-diisopropylamine; In methanol; chloroform; acetonitrile;	(d) To a solution of <strong>[74420-00-1]4-amino-1H-pyrrolo[2,3-b]pyridine</strong> (2.46 g) dissolved in acetonitrile (100 ml) was added diisopropylethylamine (6.5 ml). The mixture was stirred at 40 C. Trans-4-(1,3-dibenzyloxycarbonylguanidinomethyl)cyclohexanecarboxylic chloride (19.86 g) was added to this solution and the mixture was stirred at 50 C. for 2 hours. Then, diisopropylethylamine (6 ml) and trans-4-(1,3-dibenzyloxycarbonylguanidinomethyl)cyclohexanecarboxylic chloride (15.03 g) were added thereto and the mixture was stirred at 50 C. for 2 hours. The solvent was distilled away under reduced pressure and the residue obtained was dissolved in methanol (100 ml). Sodium methoxide (1.05 g) was added to this solution and the mixture was stirred under ice-cooling for 1 hour and at room temperature for 1 hour. The solvent was distilled away under reduced pressure, chloroform (200 ml) was added thereto and the mixture was washed with water. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 3.61 g of trans-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-4-(1-benzyloxycarbonylguanidinomethyl)cyclohexanecarboxamide, melting point 160-162 C.

Reference： [1]Patent: US5478838,1995,A

16
[ 74420-00-1 ]
[ 4659-45-4 ]
[ 1454838-76-6 ]

Yield	Reaction Conditions	Operation in experiment
10%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; acetonitrile; at 20℃; for 4h;	To a round-bottom flask was added <strong>[74420-00-1]1H-pyrrolo[2,3-b]pyridin-4-amine</strong> (1.00 g, 7.51 mmol), dichloromethane (50 mL), acetonitrile (10 mL) and DIPEA (1.96 mL, 11.27 mmol). 2,6-Dichlorobenzoyl chloride (1.57 g, 7.51 mmol) was added dropwise and the reaction mixture was stirred at room temperature for 4 hours. The mixture was poured into the ice-water and extracted with dichloromethane (3 x 30 mL). The combined organic extracts were washed with saturated aqueous sodium bicarbonate solution (50 mL) and brine (30 mL), and then dried over sodium sulfate and evaporated to dryness. The residue was purified by silica gel chromatography (0-10% MeOH/DCM) to afford a crude product, which was further purified by rpHPLC to afford the desired product (0.24 g, 10% yield). 1H NMR (DMSO-d6, 400 MHz,) delta 7.90 (d, J = 0.8 Hz, 1H), 7.82 - 7.62 (m, 3H), 7.52 (d, J = 0.8 Hz, 1H), 6.92 (s, 2H), 6.45 (s, 2H). LCMS (ESI) m/z = 307.2 [M+H+].

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 67,p. 175 - 187

17
4-chloro-2-(5-chloro-2-fluorophenyl)-5-cyclopropylpyridine [ No CAS ]
[ 74420-00-1 ]
N-[2-(5-chloro-2-fluorophenyl)-5-cyclopropyl-4-pyridyl]-1H-pyrrolo[2,3-b]pyridin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50 mg	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 180℃; for 0.5h;Inert atmosphere; Microwave irradiation;	4-Chloro-2-(5-chloro-2-fluoro-phenyl)-5-cyclopropyl-pyridine (200 mg, 0.709 mmol), lH-pyrrolo[2,3-b]pyridin-4-amine (189 mg, 1.41 mmol) and potassium phosphate tribasic (376 mg, 1.77 mmol) were dissolved in 1,4-dioxane (5 mL). Nitrogen gas was purged for 10 min. Then Pd2(dba)3 (33 mg, 0.035 mmol) and xantphos (21 mg, 0.035 mmol) were added and the resulting mixture was heated at 180 C in microwave reactor for 30 min. Product formation was confirmed by LCMS. Then the reaction mixture was diluted with water (50 mL) and extracted with EtOAc (2x50 mL). The combined organic layer was dried over anhydrous sodium sulfate and concentrated. The crude product was passed through reverse phase HPLC to afford 50 mg of N-[2-(5-chloro-2-fluoro-phenyl)-5-cyclopropyl-4-pyridyl]-lH-pyrrolo[2,3- b]pyridin-4-amine. 1H NMR: (400 MHz, CDC13): delta (ppm): 10.58 (bs, 1H), 8.75 (s, 1H), 8.42 (m, 2H), 7.99 (m, 1H), 7.78 (s, 1H), 7.42 (d, 1H), 7.30 (m, 1H), 7.08 (t, 1H), 6.92 (bs, 1H), 4.08 (m, 1H), 3.70 (m, 1H), 3.32 (m, 1H), 1.88 (m, 1H), 1.30 (d, 3H), 1.18 (m, 2H), 0.75 (m, 2H).

Reference： [1]Patent: WO2015/103355,2015,A1 .Location in patent: Paragraph 0250

18
6′-bromo-8′-methyl-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyridine]-1′,5′-dione [ No CAS ]
[ 74420-00-1 ]
8'-methyl-6'-(1H-pyrrolo[2,3-b]pyridin-4-ylamino)-2'H-spiro[cyclohexane-1,3'-imidazo[1,5-a]pyridine]-1',5'-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7%	With tris-(dibenzylideneacetone)dipalladium(0); palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; XPhos; In 1,4-dioxane; at 100℃; for 2h;Inert atmosphere;	To a solution of 100 mg (321 pmol) 6-bromo-8-methyl-2H-spiro[cyclohexane-1 3- imidazo[1,5-a]pyridine]-1,5-dione (GAS-No: 1849592-70-6; PGT Int. AppI. (2015), WO 2015200481) and 47 mg (353 pmol) 1 H-pyrrolo[2,3-b]pyridin-4-amine (GAS-No: 74420-00-1) in 12 mL 1 ,4-dioxane was added 314 mg cesium carbonate and the mixture was degassed and purged with argon several times. 20 mg 4,5-bis(diphenylphosphino)-9,9-dim ethylxanthene, 16 mg 2-(dicyclohexyl-phosphino)-2,4,6-triisopropylbiphenyl, 7.7 mg palladium(ll)acetate and 31 mg tris(dibenzylideneacetone)dipalladium(0) were added and the mixture was stirred at 1000 for 2 hours. The mixtu re was concentrated and the residue purified by flash chromatography (Biotage SNAP cartridge NH 28 g,methanol :dichloromethane) followed by preparative TLC (methanol :dichloromethane) to give 8 mg (7%) of the title compound.LC-MS: m/z = 364.5 [M÷H].1HNMR (400 MHz, DMSO-d6), 6 [ppm]= 1 .24 (1 H), 1 .48 (2H), 1 .57-1 .80 (5H), 2.43 (3H),3.03 (2H), 6.48 (1 H), 7.06 (1 H), 7.21 (1 H), 7.35 (1 H), 8.09 (1 H), 8.20 (1 H), 10.04 (1 H), 11.62 (1H).

Reference： [1]Patent: WO2018/134148,2018,A1 .Location in patent: Page/Page column 52; 53

19
[ 74420-00-1 ]
[ 688781-75-1 ]