74420-02-3|4-Hydroxy-7-azaindole| Ambeed

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Quality Control of [ 74420-02-3 ] Purity: 97% SDS Specification

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Product Details of [ 74420-02-3 ]

CAS No. :	74420-02-3
Formula :	C₇H₆N₂O
M.W :	134.14
SMILES Code :	OC1=C2C(=NC=C1)[NH]C=C2
MDL No. :	MFCD08272229
InChI Key :	IXIGMDXJXKDZOF-UHFFFAOYSA-N
Pubchem ID :	12646048

Safety of [ 74420-02-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 74420-02-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	9
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	2.0
Molar Refractivity	38.12
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	48.91 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.01
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	0.96
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.27
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.37
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.59
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.04

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.94
Solubility	1.53 mg/ml ; 0.0114 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.57
Solubility	3.57 mg/ml ; 0.0266 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.3
Solubility	0.668 mg/ml ; 0.00498 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.44 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.28

Application In Synthesis of [ 74420-02-3 ]

* 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 [ 74420-02-3 ]

[ 74420-02-3 ] Synthesis Path-Downstream 1~35

1
[ 506-59-2 ]
[ 74420-02-3 ]
[ 122379-60-6 ]

References: [1]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 317 - 325.

2
[ 74420-14-7 ]
[ 74420-02-3 ]

References: [1]Journal of Organic Chemistry,1980,vol. 45,p. 4045 - 4048.

3
[ 74420-02-3 ]
[ 106-49-0 ]
[ 122379-57-1 ]

References: [1]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 317 - 325.

4
[ 74420-02-3 ]
[ 106-47-8 ]
[ 122379-53-7 ]

References: [1]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 317 - 325.

5
[ 74420-02-3 ]
[ 104-94-9 ]
[ 122379-59-3 ]

References: [1]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 317 - 325.

6
[ 74420-02-3 ]
[ 100-01-6 ]
[ 122379-55-9 ]

References: [1]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 317 - 325.

7
[ 74420-02-3 ]
[ 62-53-3 ]
[ 122379-49-1 ]

References: [1]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 317 - 325.

8
[ 74420-02-3 ]
[ 371-40-4 ]
[ 122379-51-5 ]

References: [1]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 317 - 325.

9
[ 55052-28-3 ]
[ 74420-02-3 ]

References: [1]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 317 - 325.
[2]Organic Letters,2003,vol. 5,p. 5023 - 5025.

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

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

11
[ 640735-22-4 ]
[ 74420-02-3 ]

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

12
[ 74420-13-6 ]
[ 74420-02-3 ]

References: [1]Journal of Organic Chemistry,1980,vol. 45,p. 4045 - 4048.

13
[ 59661-65-3 ]
[ 74420-02-3 ]

References: [1]Journal of Organic Chemistry,1980,vol. 45,p. 4045 - 4048.

14
[ 930576-17-3 ]
[ 74420-02-3 ]
[ 930576-14-0 ]

Yield	Reaction Conditions	Operation in experiment
21%	With caesium carbonate; In N,N-dimethyl-formamide; at 20 - 60℃; for 8.5h;	To a solution of compound lH-pyrrolo[2,3-]pyridin-4-ol (0.1 mmol, 13.4 mg, prepared generally according to the procedures outlined by Thibault, C. et al.Org. Lett. 2003, 5, 5023-5025, the disclosure of which is incorporated by reference, in DMF (1 mL) was added cesium carbonate (Aldrich, 0.25 mmol, 81 mg). The mixture was stirred at room temperature for 0.5 h. To this mixture was added 2,4,5-trifluoro- iV-(l-(4-fluorophenyl)-2-oxo-l,2-dihydropyridin-3-yl)beiizamide (36 mg, 0.1 mmol). The reaction mixture was heated at 60 0C for 8 h. After the reaction mixture was cooled to room temperature, 2 mL of cold water was added. The reaction mixture was extracted with EtOAc (3 x 20 mL). The organic extracts were dried with MgSO4, concentrated in vacuo, and purified by preparative HPLC. The desired fractions were combined, concentrated in vacuo, and lyophilized to dry to give the title compound (trifluoroacetic acid salt, 10.0 mg, 21percent yield) as a white solid. 1H NMR (CD3OD) delta 8.61 (d, IH, J= 5.7 Hz), 8.26 (d, IH, J= 6.6 Hz), 8.02 (dd, IH, J= 11.0, 6.6 Hz), 7.51 (d, IH, J= 3.9 Hz), 7.29-7.25 (m, 3H), 7.36 (d, IH, J= 6.6 Hz), 7.25 (t, 2H, J= 8.8 Hz), 6.90 (d, IH, J= 6.6 Hz), 6.60 (d, IH, J= 3.3 Hz), 6.50 (t, IH, J= 7.2 Hz); MS(ESI+) m/z All..22 (M + H)+.

References: [1]Patent: WO2007/35428,2007,A1 .Location in patent: Page/Page column 36.

15
[ 71-23-8 ]
[ 74420-02-3 ]
[ 1011711-58-2 ]

References: [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 737 - 751.

16
[ 64-17-5 ]
[ 74420-02-3 ]
[ 1011711-57-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃;Inert atmosphere;	4-Ethoxy-1H-pyrrolo[2,3-b]pyridineDiethyl azodicarboxylate (DEAD) (520 mul, 3.3 mmol) is added dropwise, at ambient temperature and under an inert atmosphere, to a solution of PPh3 (1.04 g, 3.96 mmol) in anhydrous THF (13 ml). This solution is transferred via a tube, under an inert atmosphere, into a round-bottomed flask containing a solution of <strong>[74420-02-3]4-hydroxy-7-azaindole</strong> (222 mg, 1.65 mmol) and ethanol (115 mul, 1.98 mmol) in anhydrous tetrahydrofuran (THE) (41 ml). The solution is stirred at ambient temperature for 2 h. The solvent is evaporated. The residue obtained is purified with a chromatography column (eluent: CH2Cl2/MeOH 98:2) to give the desired compound (214 mg, 80percent). Solid; M.p.=176-178° C. (Et2O); 1H NMR (300 MHz, CDCl3) delta 1.52 (t, 3H, J=7.1 Hz, CH3), 4.26 (q, 2H, J=7.1 Hz, CH2), 6.53 (d, 1H, J=5.6 Hz, Harom), 6.59 (broad s, 1H, Harom), 7.18 (broad s, 1H, Harom), 8.18 (d, 1H, J=5.6 Hz, Harom), 9.64 (broad s, 1H, NH); MS (SI) m/z 163 (M+H+).

References: [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 737 - 751.
[2]Patent: US2010/184790,2010,A1 .Location in patent: Page/Page column 5.

17
[ 74420-02-3 ]
[ 67-63-0 ]
[ 937797-32-5 ]

References: [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 737 - 751.

18
[ 400-74-8 ]
[ 74420-02-3 ]
4-[4-nitro-2-(trifluoromethyl)phenoxy]-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	With potassium carbonate; In dimethyl sulfoxide; at 20℃; for 1.0h;	A solution of 1-fluoro-4-nitro-2-(trifluoromethyl)benzene (5.3 mL, 38 mmol) and <strong>[74420-02-3]1H-pyrrolo[2,3-b]pyridin-4-ol</strong> (CAS No. [74420-02-3]; 4.67 g, 34.8 mmol) in DMSO (110 mL) was treated withpotassium carbonate (19.2 g, 139 mmol) and stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate (200 mL) and washed with two times with 20 mL water and brine (20 mL), dried with sodium sulfate and concentrated in vacuo. The resulting residue was purified via a Biotage chromatography system (bOg snap KP-Silcolumn, hexane I 20 ? 100percent ethyl acetate) to obtain 4.62 g (96 percent purity, 39 percent yield) of thedesired title compound.1HNMR (400 MHz, DMSO-d6) delta [ppm]: 6.11 (d, 1H), 6.92 (d, 1H), 7.25 (d, 1H), 7.48 (d, 1H),8.28 (d, 1 H), 8.46 (dd, 1 H), 8.58 (d, 1 H), 12.05 (br s, 1 H).
39%	With potassium carbonate; In dimethyl sulfoxide; at 20℃; for 1.0h;	A solution of 1 -fluoro-4-nitro-2-(trifluoromethyl)benzene (5.3 mL, 38 mmol) and 1 /-/-pyrrolo[2,3- b]pyridin-4-ol (CAS No. [74420-02-3]; 4.67 g, 34.8 mmol) in DMSO (1 10 mL) was treated with potassium carbonate (19.2 g, 139 mmol) and stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate (200 mL) and washed with two times with 20 mL water and brine (20 mL), dried with sodium sulfate and concentrated in vacuo. The resulting residue was purified via a Biotage chromatography system (100g snap KP-Sil column, hexane / 20 - 100percent ethyl acetate) to obtain 4.62 g (96 percent purity, 39 percent yield) of the desired title compound. 1H-NMR (400 MHz, DMSO-d6) delta [ppm]: 6.1 1 (d, 1 H), 6.92 (d, 1 H), 7.25 (d, 1 H), 7.48 (d, 1 H), 8.28 (d, 1 H), 8.46 (dd, 1 H), 8.58 (d, 1 H), 12.05 (br s, 1 H).

References: [1]Patent: WO2018/228923,2018,A1 .Location in patent: Page/Page column 60.
[2]Patent: WO2019/16071,2019,A1 .Location in patent: Page/Page column 194.

19
[ 74420-02-3 ]
4-[4-nitro-2-(trifluoromethyl)phenoxy]-1-[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

References: [1]Patent: WO2018/228923,2018,A1 .

20
[ 74420-02-3 ]
3-chloro-4-[4-nitro-2-(trifluoromethyl)phenoxy]-1-[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

References: [1]Patent: WO2018/228923,2018,A1 .

21
[ 74420-02-3 ]
4-[(3-chloro-1-[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3-(trifluoromethyl)aniline [ No CAS ]

References: [1]Patent: WO2018/228923,2018,A1 .

22
[ 66684-58-0 ]
[ 74420-02-3 ]
4-(2,6-difluoro-4-nitrophenoxy)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With potassium carbonate; In dimethyl sulfoxide; at 20℃; for 1.0h;	A solution of 1 ,2,3-trifluoro-5-nitrobenzene (CAS No. [66684-58-0]; 3.59 g, 20.3 mmol) and 1 H- pyrrolo[2,3-b]pyridin-4-ol (CAS No. [74420-02-3]; 1 .10 eq., 2.99 g, 22.3 mmol) in DMSO (65 mL) was treated with potassium carbonate (4.00 eq, 1 1 .2 g, 81.1 mmol) and stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate (500 mL) and washed with water (3 x 200 mL) and brine (150 mL), dried with sodium sulfate and concentrated in vacuo. The obtained material was purified by flash chromatography (S1O2- hexane/ ethyl acetate) to give the title compound (3.1 g, 52percent). LC-MS (method 2): Rt = 1 .13 min; MS (ESIpos): m/z = 292 [M+H]+. 1H-NMR (400 MHz, DMSO-d6) delta [ppm] = 6.35 (d, 1 H), 6.59 (d, 1 H), 7.47 (d, 1 H), 8.13 (d, 1 H), 8.37 - 8.43 (m, 2H), 1 1 .97 (br s, 1 H).
52%	With potassium carbonate; In dimethyl sulfoxide; at 20℃; for 1.0h;	A solution of 1 ,2,3-trifluoro-5-nitrobenzene (CAS No. [66684-58-0]; 3.59 g, 20.3 mmol) and 1 H- pyrrolo[2,3-b]pyridin-4-ol (CAS No. [74420-02-3]; 1 .10 eq., 2.99 g, 22.3 mmol) in DMSO (65 mL) was treated with potassium carbonate (4.00 eq, 1 1.2 g, 81.1 mmol) and stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate (500 mL) and washed with water (3 x 200 mL) and brine (150 mL), dried with sodium sulfate and concentrated in vacuo. The obtained material was purified by flash chromatography (S1O2- hexane/ ethyl acetate) to give the title compound (3.1 g, 52percent). LC-MS (Method 2): Rt = 1 .13 min; MS (ESIpos): m/z = 292 [M+H]+. 1H-NMR (400 MHz, DMSO-d6) delta [ppm] = 6.35 (d, 1 H), 6.59 (d, 1 H), 7.47 (d, 1 H), 8.13 (d, 1 H), 8.37 - 8.43 (m, 2H), 1 1 .97 (br s, 1 H).

References: [1]Patent: WO2018/228920,2018,A1 .Location in patent: Page/Page column 187.
[2]Patent: WO2019/16071,2019,A1 .Location in patent: Page/Page column 105.

23
[ 74420-02-3 ]
4-(2,6-difluoro-4-nitrophenoxy)-1-[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine [ No CAS ]