[ CAS No. 67058-71-3 ]

Name: 67058-71-3|1-(1H-Pyrrolo[2,3-c]pyridin-3-yl)ethanone|97%
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SKU: A100277
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Quality Control of [ 67058-71-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 67058-71-3 ]

SDS Specification

Alternatived Products of [ 67058-71-3 ]

Product Details of [ 67058-71-3 ]

CAS No. :	67058-71-3	MDL No. :	MFCD11848707
Formula :	C₉H₈N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VVNOWWBAXYETQZ-UHFFFAOYSA-N
M.W :	160.17 g/mol	Pubchem ID :	11829729
Synonyms :

Calculated chemistry of [ 67058-71-3 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.11
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	46.29
TPSA :	45.75 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) :	-6.81 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.1
Log Po/w (XLOGP3) :	0.66
Log Po/w (WLOGP) :	1.77
Log Po/w (MLOGP) :	0.0
Log Po/w (SILICOS-IT) :	2.32
Consensus Log Po/w :	1.17

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.74
Solubility :	2.93 mg/ml ; 0.0183 mol/l
Class :	Very soluble
Log S (Ali) :	-1.2
Solubility :	10.2 mg/ml ; 0.0636 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.23
Solubility :	0.0932 mg/ml ; 0.000582 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.49

Safety of [ 67058-71-3 ]

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

Application In Synthesis of [ 67058-71-3 ]

* 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.

Upstream synthesis route of [ 67058-71-3 ]
Downstream synthetic route of [ 67058-71-3 ]

[ 67058-71-3 ] Synthesis Path-Upstream 1~1

1
[ 271-29-4 ]
[ 75-36-5 ]
[ 67058-71-3 ]

Reference： [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 6, p. 2834 - 2844
[2] Journal of Organic Chemistry, 2002, vol. 67, # 17, p. 6226 - 6227

[ 67058-71-3 ] Synthesis Path-Downstream 1~10

2
[ 271-29-4 ]
[ 75-36-5 ]
[ 67058-71-3 ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 2834 - 2844
[2]Journal of Organic Chemistry,2002,vol. 67,p. 6226 - 6227

3
[ 5292-43-3 ]
[ 67058-71-3 ]
[ 1386457-04-0 ]

Yield	Reaction Conditions	Operation in experiment
		To a suspension of NaH (60 % in mineral oil, 90 mg, 2.25 mmol) in DMF (4.2 mL) cooled at 0C was added a solution of 1-(1 H-pyrrolo[2,3-c]pyridin-3-yl)-ethanone (prepared according to J. Org. Chem. 2002, 67, 6226) (300 mg, 1.87 mmol) in DMF (4.2 mL) and the resulting suspension was stirred at 0C under nitrogen atmosphere for 30 min before slow addition of tert-butyl bromoacetate (277 mu, 1.87 mmol). The reaction mixture was allowed to reach RT and further stirred at RT for 1.5 h. After completion of the reaction, the mixture was purified first by catch-release on SiliaPrep Tosic Acid-(2x10 g) (Varian) (eluent: MeOH (50 mL) by 2 M ammonia in MeOH (50 mL)) to give a mixture of regioisomers: (3-acetyl-pyrrolo[2,3-c]pyridin- 1-yl)-acetic acid tert-butyl ester and (3-acetyl-pyrrolo[2,3-c]pyridin-6-yl)-acetic acid tert-butyl ester followed by flash column chromatography on silica gel (CH2CI2 to CH2CI2/MeOH 85-15) to give (3-acetyl-pyrrolo[2,3-c]pyridin-1-yl)-acetic acid tert-butyl ester as a yellow powder. TLC, Rf (CH2CI2/ MeOH 9-1) = 0.50; MS (UPLC/MS): 275.3 [M+H]+, 319.2 [M+HCOO]-; tR (HPLC conditions f): 1.28 min; 1 H-NMR (400 MHz, DMSO-d6): delta (ppm): 8.88 (s, 1 H), 8.50 (s, 1 H), 8.33 (d, 1 H), 8.06 (d, 1 H), 5.27 (s, 2H), 2.48 (s,3H), 1.45 (s, 9H).

Reference： [1]Patent: WO2012/93101,2012,A1 .Location in patent: Page/Page column 134-135

4
[ 67058-71-3 ]
[ 1386457-06-2 ]

Reference： [1]Patent: WO2012/93101,2012,A1

5
[ 67058-71-3 ]
(Z)-2-chloro-3-(dimethylamino)-1-(1-(phenylsulfonyl)-1H-pyrrolo[2,3-c]pyridin-3-yl)prop-2-en-1-one [ No CAS ]