[ CAS No. 63674-48-6 ] {[proInfo.proName]}

Name: 63674-48-6|1-(2,6-Dimethylphenyl)-5-oxopyrrolidine-3-carboxylic acid|95%
Brand: Ambeed
SKU: A499682
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Quality Control of [ 63674-48-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 63674-48-6 ]

SDS Specification

Alternatived Products of [ 63674-48-6 ]

Product Details of [ 63674-48-6 ]

CAS No. :	63674-48-6	MDL No. :	MFCD05096196
Formula :	C₁₃H₁₅NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PMFQUYSCBXNYOR-UHFFFAOYSA-N
M.W :	233.26	Pubchem ID :	4739040
Synonyms :

Calculated chemistry of [ 63674-48-6 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.38
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	67.79
TPSA :	57.61 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.84 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.6
Log Po/w (XLOGP3) :	1.25
Log Po/w (WLOGP) :	1.36
Log Po/w (MLOGP) :	1.59
Log Po/w (SILICOS-IT) :	1.91
Consensus Log Po/w :	1.54

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.85

Water Solubility

Log S (ESOL) :	-2.2
Solubility :	1.46 mg/ml ; 0.00627 mol/l
Class :	Soluble
Log S (Ali) :	-2.06
Solubility :	2.04 mg/ml ; 0.00875 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.66
Solubility :	0.514 mg/ml ; 0.0022 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.2

Safety of [ 63674-48-6 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P280-P305+P351+P338	UN#:
Hazard Statements:	H302-H317	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 63674-48-6 ]

* 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 [ 63674-48-6 ]

[ 63674-48-6 ] Synthesis Path-Downstream 1~50

1
[ 97-65-4 ]
[ 87-62-7 ]
[ 63674-48-6 ]

Yield	Reaction Conditions	Operation in experiment
70%	at 130℃; for 0.75h;	1.a Example 1: Synthesis of l-(2,6-dimethyIphenyl)-3-isopropyl-5-oxo-pyrrolidine-3- carboxylic acid [3,5-bis(trifluoromethyl)phenyl] amidestep e step d[0072] a) A mixture of 2,6-dimethylaniline (121 g, 1 mol) and itaconic acid (130 g, 1 mol) was heated to 130 °C for 45 min in a flask open to the atmosphere, letting the generated steam vent. The heating source was removed and 0.8 L of ethyl acetate was added under vigorous stirring, while the mixture was still hot (allowing initially for some reflux). The mixture was then let to cool to room temperature while stirring. The solids were filtered off, washed with 0.4 L of ethyl acetate and dried in air to give 164 g (70% yield) of colorless crystals. LC-MS Rt (retention time): 0.54 min, MS: (ES) mlz 234 (M+H+).

Reference： [1]Current Patent Assignee: CHEMOCENTRYX INC - WO2011/35332, 2011, A1 Location in patent: Page/Page column 25-26

2
[ 63674-48-6 ]
[ 75-65-0 ]
[ 1242179-00-5 ]

Yield	Reaction Conditions	Operation in experiment
81%	With dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine In dichloromethane at 10 - 20℃; for 14h; Cooling with ice;	31 Example 31: Synthesis of tert-butyl l-(2,6-dimethyIphenyl)-5-oxopyrrolidine-3- carboxylate[0169] a) To a 2 L, 3-neck flask was added l-(2,6-dimethylphenyl)-5-oxopyrrolidine-3- carboxylic acid (93 g, 0.40 mol), anhydrous tert-butanol (60 mL, 0.63 mol), TEA (110 mL, 0.79 mol), DMAP (5.0 g, 41 mmol), and CH2C12 (800 mL). After the mixture was cooled in an ice bath under nitrogen atmosphere with mechanical stirring, 2,4,6-trichlorobenzoyl chloride (108 g, 0.443 mol) was added in portions over the course of 15 minutes such that the temperature did not exceed 10 °C. After the addition was complete, the ice bath was removed, the mixture was allowed to warm to room temperature and stirred for an additional 14 h. TLC and LCMS indicated complete consumption of starting material and formation of desired product. The mixture was filtered and the filter cake was washed with EtOAc (100 mL) and ether (150 mL). The filtrate was washed with two 200 mL portions of 1 MNaHS04, four 200 mL portions of saturated aqueous NaHC03, and brine (100 mL). After drying over MgS04, the organic phase was treated with 24 g of silica gel, and filtered. The filtrate was concentrated to 250 mL and diluted with hexane. A crystalline precipitate began to form, and an initial crop of 66 g was recovered. The filtrate was recovered andrecrystallized (ether/hexanes) to afford a second crop (27 g); overall yield, 93 g (81%). LCMS Rt (retention time): 2.28 min, MS: (ES) m/z 290 (M+H+).

Reference： [1]Current Patent Assignee: CHEMOCENTRYX INC - WO2011/35332, 2011, A1 Location in patent: Page/Page column 70

3
[ 67-56-1 ]
[ 63674-48-6 ]
[ 149-73-5 ]
[ 1280200-63-6 ]

Yield	Reaction Conditions	Operation in experiment
99%	With acetyl chloride at 64℃; for 1h;	1.b [0073] b) Acetyl chloride (2.40 g, 30.9 mmol) was added dropwise to 400 mL of methanol. l-(2,6-dimethylphenyl)-5-oxo-pyrrolidine-3-carboxylic acid (144 g, 618 mmol, prepared in step a above) was added to the solution followed by trimethyl ortho formate (67 mL, 618 mmol). he mixture was heated to 64 °C for 1 h and then concentrated in vacuo to give 152 g (99% yield) of pure product as an oil. LC-MS Rt (retention time): 1.49 min, MS: (ES) mlz 248 (M+H+).

Reference： [1]Current Patent Assignee: CHEMOCENTRYX INC - WO2011/35332, 2011, A1 Location in patent: Page/Page column 26

4
[ 63674-48-6 ]
[ 1280201-02-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: dmap; triethylamine; 2,4,6-trichlorobenzoyl chloride / dichloromethane / 14 h / 10 - 20 °C / Cooling with ice 2.1: lithium hexamethyldisilazane / tetrahydrofuran / -50 - 0 °C 2.2: 2 h / 0 - 20 °C 3.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / <i>tert</i>-butyl alcohol; tetrahydrofuran / 18 h / 20 °C 4.1: sodium periodate / water; tetrahydrofuran / 20 °C 5.1: ammonium acetate; acetic acid / tetrahydrofuran; methanol / 40 °C