[ CAS No. 800401-84-7 ] {[proInfo.proName]}

Name: 800401-84-7|5-Chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid|95%
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SKU: A200847
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Quality Control of [ 800401-84-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 800401-84-7 ]

Product Details of [ 800401-84-7 ]

CAS No. :	800401-84-7	MDL No. :	MFCD21607077
Formula :	C₈H₅ClN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YMSGAOPCRLRFMT-UHFFFAOYSA-N
M.W :	196.59	Pubchem ID :	44630705
Synonyms :

Calculated chemistry of [ 800401-84-7 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	48.06
TPSA :	65.98 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) :	-6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.2
Log Po/w (XLOGP3) :	1.8
Log Po/w (WLOGP) :	1.91
Log Po/w (MLOGP) :	1.17
Log Po/w (SILICOS-IT) :	2.0
Consensus Log Po/w :	1.62

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.64
Solubility :	0.451 mg/ml ; 0.0023 mol/l
Class :	Soluble
Log S (Ali) :	-2.8
Solubility :	0.308 mg/ml ; 0.00157 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.9
Solubility :	0.245 mg/ml ; 0.00124 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.59

Safety of [ 800401-84-7 ]

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 [ 800401-84-7 ]

* 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 [ 800401-84-7 ]
Downstream synthetic route of [ 800401-84-7 ]

[ 800401-84-7 ] Synthesis Path-Upstream 1~2

1
[ 127-17-3 ]
[ 211308-81-5 ]
[ 800401-84-7 ]

Reference： [1] Patent: WO2006/59164, 2006, A2, . Location in patent: Page/Page column 21
[2] Patent: WO2004/104001, 2004, A2, . Location in patent: Page 51

2
[ 1072-98-6 ]
[ 800401-84-7 ]

Reference： [1] Patent: WO2004/104001, 2004, A2,

[ 800401-84-7 ] Synthesis Path-Downstream 1~17

1
[ 800401-84-7 ]
(S)-2-Amino-3-(4-fluoro-phenyl)-1-(4-hydroxy-piperidin-1-yl)-propan-1-one hydrochloride [ No CAS ]
5-chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid [1-(S)-(4-fluorobenzyl)-2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In ethanol; at 20.0℃; for 16.0h;	5-Chloro-lH-pyrrolo [2,3-b] pyridine-2-carboxylic acid (Preparation 57, 50MG, 0. 25mmol), 2-(S)-amino-3-(4-fluorophenyl)-1-(4-hydroxypiperidin-1- yl) propan-l-one hydrochloride (85mg, 0. 25MMOL) and DMTMM (85mg, 0. 31MMOL) were dissolved in ethanol (5ML) and 4-methylmorpholine (31mul, 0. 28MMOL). The reaction mixture was stirred at rt for 16h. The solvent was removed in vacuo and the residue partitioned between water (30ML) and EtOAc (3 x 25ML). The combined organics were dried (MgSO4), concentrated in vacuo and purified by chromatography on silica gel eluting with methanol : dichloromethane (1: 19) to give the title compound as a beige solid. m/z (ES+) = 445 [M+ H] + ; RT = 3. 31min.

Reference： [1]Patent: WO2004/104001,2004,A2 .Location in patent: Page 109

2
[ 800401-84-7 ]
[ 123665-42-9 ]
5-chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid (1-dimethylcarbamoyl-2-(S)-phenylethyl)amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In ethanol; at 20.0℃; for 24.0h;	5-Chloro-lH-pyrrolo [2,3-b] pyridine-2-carboxylic acid (Preparation 57, 55MG, 0. 28MMOL), 2-(S)-amino-N,N-dimethyl-3-phenylpropionamide hydrochloride (70mg, 0. 31MMOL) and DMTMM (93mg, 0.34mmol) were dissolved in ethanol (5ML) and 4-methylmorpholine (341, 0. 31MMOL). The reaction mixture was stirred at rt for 24h. The solvent was removed III vacuo and the residue partitioned between water (40ML) and EtOAc (2 x 40ML). The combined organics were washed with 2N NAOH solution (40ML), brine (40ML), dried (MgS04), concentrated IFS vacuo and purified by chromatography on silica gel eluting with methanol: dichloromethane (3: 97) to give the title compound as a yellow solid. m/z (ES+) = 371 [M+ H] + ; RT = 3. 49MIN.

Reference： [1]Patent: WO2004/104001,2004,A2 .Location in patent: Page 109-110

3
[ 127-17-3 ]
[ 211308-81-5 ]
[ 800401-84-7 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,4-diaza-bicyclo[2.2.2]octane;palladium diacetate; In N,N-dimethyl-formamide; at 110.0℃; for 16.0h;	Preparation 5 : 5-Chloro-l/T-pyrrolo[2,3-b]pyridine-2-carboxylic acid; Pyruvic acid (0.43ml, 6.24mmol) was added to a solution of 5-chloro-3-iodopyridin-2-ylamine (Preparation 4, 500mg, 2.08mmol), palladium acetate (23mg, O.lOmmol) and DABCO (700mg, 6.24mmol) in anhydrous DMF (2OmL). The reaction mixture was degassed with argon for 20min, then heated to HO0C for 16h. The solvent was removed in vacuo and the residue suspended in water (1OmL) and acetic acid (5mL) and then filtered. The solid was dissolved in EtOAc (5OmL), extracted into 2N NaOH solution (5OmL) and the organic layer discarded. The aqueous solution was acidified with concentrated HCl and extracted into EtOAc (2x40mL). The combined organics were dried (MgSO4) and concentrated in vacuo to give the title compound as a beige solid. deltaH (CD3OD): 7.14 (IH, s), 8.14 (IH, d), 8.35 (IH, d).
	With 1,4-diaza-bicyclo[2.2.2]octane;palladium diacetate; In DMF (N,N-dimethyl-formamide); at 110.0℃; for 16.0h;	Pyruvic acid (0. 43ML, 6. 24MMOL) was added to a solution of 5-chloro-3- iodopyridin-2-ylamine (Preparation 56, 500MG, 2.08mmol), palladium acetate (23mg, 0. 10MMOL) and DABCO (700mg, 6. 24MMOL) in anhydrous DMF (20ml). The reaction mixture was degassed with argon for 20min, then heated to 110C for 16h. The solvent was removed in vacuo and the residue suspended in water (lOml) and acetic acid (5ML) and then filtered. The solid was dissolved in EtOAc (50ML), extracted into 2N NAOH solution (50ML) and the organic layer discarded. The aqueous solution was acidified with concentrated HC1 and extracted into EtOAc (2 x 40ML). The combined organics were dried (MgS04) and concentrated in vacuo to give the title compound as a beige solid. aH (CD30D): 7.14 (1H, s), 8.14 (1H, d), 8.35 (1H, d).

Reference： [1]Patent: WO2006/59164,2006,A2 .Location in patent: Page/Page column 21
[2]Patent: WO2004/104001,2004,A2 .Location in patent: Page 51

4
[ 800401-84-7 ]
[ 800402-04-4 ]
5-chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid [1-(S)-(4-fluorobenzyl)-2-(3-hydroxypyrrolidin-1-yl)-2-oxoethyl]amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20.0℃; for 16.0h;	To a solution OF 5-CHLORO-LH-PYRROLO [2,3-b] pyridine-2-carboxylic acid (Preparation 57,34mg, 0. 17MMOL) in DMF (5ML) was added 2- (S)-AININO-3- (4- FLUOROPHENYL)-1- (3- ()-HYDROXYPYRROLIDIN-1-YL) PROPAN-1-ONE hydrochloride (Preparation 103, 50MG, 0. 17MMOL), HOBt (23mg, 0. 17MMOL) and DIPEA (94PL, 0. 54MMOL). After 5MIN, EDCI (43mg, 0. 23MMOL) was added and the reaction stirred at rt for 16h. The solvent was removed in vacuo and the residue partitioned between water (25mL) and ethyl acetate (3 x 20mL). The combined organic layer was washed with 2N sodium hydroxide solution (2 x LOML), brine (lOmL), dried (MGS04) and concentrated in vacuo. Purification via chromatography on silica gel eluting with methanol: dichloromethane (7: 93) GAVETHETITLECOMPOUND. M/Z (ES+) =431 [M+ H] + ; RT = 3. 49MIN.

Reference： [1]Patent: WO2004/104001,2004,A2 .Location in patent: Page 155

5
[ 800401-84-7 ]
[ 800402-11-3 ]
2-(S)-[(5-chloro-1H-pyrrolo[2,3-b]pyridine-2-carbonyl)amino]-3-(4-fluorophenyl)propionic acid tert-butyl eter [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20.0℃; for 72.0h;	To a solution OF 5-CHLORO-LH-PYRROLO [2,3-b] PYRIDINE-2-CARBOXYLIC acid (Preparation 57, 500MG, 2.54mmol) in DMF (20mL) was added 2- (S)-AMINO-3- (4- fluorophenyl) propionic acid tert-butyl ester hydrochloride (Preparation 114,701mg, 2.54mmol), HOBt (344mg, 2. 54MMOL) and DIPEA (1. 4mL, 7. 88MMOL). After 5MIN, EDCI (634mg, 3. 31MMOL) was added and the reaction mixture stirred at rt for 72H. The solvent was removed IRA vacuo and the solid partitioned between water (50ML) and ethyl acetate (3 x 40mL). The combined organic phase was washed with brine (20mL), dried (MGS04), concentrated in vacuo and purified by chromatography on silica gel eluting with methanol: dichloromethane (1: 99) to give the title compound. ON (CD30D): 1.42 (9H, s), 3.09 (1H, dd), 3.22 (1H, dd), 4.76 (1H, m), 6.98 (2H, m), 7.07 (1H, s), 7.27 (2H, m), 8. 06 (1H, d), 8.28 (1H, d); M/Z (ES+) = 418 [M+ H] +.

Reference： [1]Patent: WO2004/104001,2004,A2 .Location in patent: Page 154

6
[ 800401-84-7 ]
[ 5468-37-1 ]
5-chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid (2-oxo-2-phenylethyl)amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In tetrahydrofuran; at 20.0℃; for 16.0h;	5-Chloro-lH-pyrrolo [2, 3-B] PYRIDINE-2-CARBOXYLIC acid (Preparation 57, 50MG, 0. 25MMOL), 2-aminoacetophenone hydrochloride (48mg, 0.28mmol) and DMTMM (85mg, 0. 31mmol) were dissolved in THF (5mL) and 4-METHYLMORPHOLINE (31muL, 0. 28MMOL). The reaction mixture was stirred at rt for 16h. The solvent was removed in vacuo and the residue partitioned between water (20mL) and EtOAc (3 x 20mL). The combined organics were dried (MGS04), concentrated in vacuo and purified by chromatography on silica gel eluting with methanol : dichloromethane (1: 19) to give the title compound. m/z (ES+) = 314 [M+ H] + ; RT = 3. 47MIN.

Reference： [1]Patent: WO2004/104001,2004,A2 .Location in patent: Page 155-156

7
[ 800401-84-7 ]
C₁₇H₁₅ClIN₅O₂ [ No CAS ]