[ CAS No. 273404-37-8 ] {[proInfo.proName]}

Name: 273404-37-8|(S)-1-((S)-2-(4-Amino-3-chlorobenzamido)-3,3-dimethylbutanoyl)-N-((2R,3S)-2-ethoxy-5-oxotetrahydrofuran-3-yl)pyrrolidine-2-carboxamide|99%
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2D 3D

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Quality Control of [ 273404-37-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 273404-37-8 ]

SDS Specification

Alternatived Products of [ 273404-37-8 ]

Product Details of [ 273404-37-8 ]

CAS No. :	273404-37-8	MDL No. :	MFCD23102811
Formula :	C₂₄H₃₃ClN₄O₆	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SJDDOCKBXFJEJB-MOKWFATOSA-N
M.W :	509.00	Pubchem ID :	11398092
Synonyms :	Belnacasan

Calculated chemistry of [ 273404-37-8 ]

Physicochemical Properties

Num. heavy atoms :	35
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.58
Num. rotatable bonds :	11
Num. H-bond acceptors :	6.0
Num. H-bond donors :	3.0
Molar Refractivity :	133.66
TPSA :	140.06 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-7.74 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.19
Log Po/w (XLOGP3) :	2.35
Log Po/w (WLOGP) :	1.48
Log Po/w (MLOGP) :	1.19
Log Po/w (SILICOS-IT) :	2.02
Consensus Log Po/w :	2.05

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	2.0
Egan :	1.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.88
Solubility :	0.0675 mg/ml ; 0.000133 mol/l
Class :	Soluble
Log S (Ali) :	-4.93
Solubility :	0.00597 mg/ml ; 0.0000117 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.7
Solubility :	0.0102 mg/ml ; 0.00002 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	4.69

Safety of [ 273404-37-8 ]

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

Application In Synthesis of [ 273404-37-8 ]

* 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 [ 273404-37-8 ]

[ 273404-37-8 ] Synthesis Path-Downstream 1~10

1
[ CAS Unavailable ]
[ CAS Unavailable ]
[ 273404-37-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In DMF (N,N-dimethyl-formamide); water; ethyl acetate at 0 - 25℃; for 6.5 - 8h;	6.3 Separately, 23.5 g of N-Methylmorpholine is added to a mixture of 33.1 g of 4-Amino-chloro-benzoic acid 34.4 g of 2- Chloro-4,6-dimethoxytriazine (DMT-Cl) in 300 ml of ethyl acetate over 20-30 minutes at ambient temperature for 2-3 hours at 23- 27°C to obtain the DMT active ester of 4-Amino-3-chlorobenzoic acid. The mixture is cooled to 0° to +5°C and 30 0 ml of purified water are added to the solution keeping temperature in the same range. The solution of the deprotected t-leucirae product as the citrate salt is added at 0°C to +5°C over 30-60 minutes, the reaction mixture is then brought to pH 6.5-7. 5 by adding 30% sodium hydroxide (approx. amount: 71 ml), and stirred 6-7 hrs at 20° to 25°C. After completion of the reaction, the phases are separated and the organic layer added to sodium bisulfate solution (15 g of sodium bisulfate in 235 ml of water) and stirred for 3 hrs at 20°C to 25°C. The phases azre separated and the organic layer is washed four times with water (150 ml each), twice with sodium bicarbonate solution (total: 20 g of sodium bicarbonate in 400 ml of water), and once with 1 50 ml of water. To the solution is added 10 g of activated charcoal and 10 g of Dicalite and filtered and the solids washed with 100 ml of ethyl acetate. The filtrate was distilled under vacuum to a volume of 200 ml at < 40°C when the resultant mixture crystallizes. Ethyl acetate (150 ml) was added to a total volume of 350 ml. N- heptane (300 ml) was added over 2 hrs and after stirring the slurry for 3 hrs at 20° to 25°, the solid was filtered, washed with ethyl acetate/N-Heptane (100 ml, 1: 1) and dried at 60°C under vacuum.

Reference： [1]Current Patent Assignee: VERTEX PHARMACEUTICALS (OLD) - WO2005/90334, 2005, A2 Location in patent: Page/Page column 77-78

2
[ 865839-06-1 ]
[ 2486-71-7 ]
(S)-1-((S)-2-[1-(4-amino-3-chlorophenyl)methanoyl]amino}-3,3-dimethylbutanoyl)pyrrolidine-2-carboxylic acid ((2R,3S)-2-ethoxy-5-oxo-tetrahydrofuran-3-yl)amide [ No CAS ]

Reference： [1]Organic Letters,2008,vol. 10,p. 185 - 188

3
[ 62965-10-0 ]
(S)-1-((S)-2-[1-(4-amino-3-chlorophenyl)methanoyl]amino}-3,3-dimethylbutanoyl)pyrrolidine-2-carboxylic acid ((2R,3S)-2-ethoxy-5-oxo-tetrahydrofuran-3-yl)amide [ No CAS ]

Reference： [1]Patent: US9487555,2016,B2

4
[ 374773-66-7 ]
[ 273404-37-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 10% Pd/C; hydrogen / methanol; ethyl acetate / 18 h 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 18.67 h / 0 - 20 °C 3: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere 4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 18.17 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: VERTEX PHARMACEUTICALS (OLD) - US9487555, 2016, B2

5
[ 2486-71-7 ]
(S)-1-((S)-2-[1-(4-amino-3-chlorophenyl)methanoyl]amino}-3,3-dimethylbutanoyl)pyrrolidine-2-carboxylic acid ((2R,3S)-2-ethoxy-5-oxo-tetrahydrofuran-3-yl)amide [ No CAS ]

Reference： [1]Patent: US9487555,2016,B2

6
[ 374773-69-0 ]
[ 273404-37-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 18.17 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: VERTEX PHARMACEUTICALS (OLD) - US9487555, 2016, B2

7
[ 410079-22-0 ]
[ 374773-70-3 ]
[ 273404-37-8 ]

Yield	Reaction Conditions	Operation in experiment
11.2 g	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 18.17h;	Synthesis of 1-[2-(4-amino-3-chlorobenzoylamino)-3,3-dimethylbutyryl]pyrrolidine-2-carboxylic acid (2-ethoxy-5-oxotetrahydrofuran-3-yl)amide (I-A) Synthesis of 1-[2-(4-amino-3-chloro-benzoylamino)-3,3-dimethyl-butyryl]-pyrrolidine-2-carboxylic acid (2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-amide (I-A) ;To a solution of 6 (5.05 g, 22.0 mmol) in CH2Cl2 (50 mL) at 0° C. was added 1,3-dimethylbarbituric acid (DMBA) (3.78 g, 24.2 mmol) and Pd(PPh3)4 (0.15 g, 0.13 mmol). After 10 minutes, a solution of 5 (8.40 g, 22.0 mmol) in DMF (25 mL) was added followed by diisopropylethylamine (DIPEA) (7.66 mL, 44.1 mmol), (2.98 g, 22.0 mmol) and EDC (5.06 g, 26.4 mmol). The solution was stirred at 0° C. for 10 minutes then at room temperature for 18 hours. The reaction was diluted with EtOAc (200 mL), washed with 0.5N NaHSO4 (2200 mL), 10% NaHCO3 (2200 mL), saturated NaCl (1*150 mL), dried over anhydrous MgSO4, and evaporated to dryness. Flash column chromatography on silica gel using CH2Cl2/MeOH, (99/1 to 98/2%) afforded the title compound as a white solid (11.20 g, 77% yield): 1H-NMR (500 MHz, CDCl3) δ 1.08 (s, 9H), 1.27 (t, 3H), 1.85-1.99 (m, 1H), 2.00-2.06 (m. 1H), 2.07-2.18 (m, 1H), 2.32-2.48 (m, 2H), 2.78-2.89 (m, 1H), 3.62-3.76 (m, 2H), 3.82-3.96 (m, 2H), 4.39 (s, 1H), 4.54-4.60 (m, 1H), 4.62-4.76 (m, 1H), 4.85 (d, 1H), 6.57 (d, 1H), 6.73 (d, 1H), 7.38 (d, 1H), 7.49 (d, 1H), 7.72 (s, 1H). Analytical HPLC (cyano column): 13.10 min. LC-MS (ES+) m/e=509.4 (M+H), m.p.=96-99° C.

Reference： [1]Current Patent Assignee: VERTEX PHARMACEUTICALS (OLD) - US9487555, 2016, B2 Location in patent: Page/Page column 16

8
[ 1230628-85-9 ]
[ 273404-37-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 18.67 h / 0 - 20 °C 2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere 3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 18.17 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: VERTEX PHARMACEUTICALS (OLD) - US9487555, 2016, B2

9
[ 220184-67-8 ]
[ 273404-37-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / dichloromethane / 0.17 h / 0 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 18.17 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: VERTEX PHARMACEUTICALS (OLD) - US9487555, 2016, B2

10
[ 20859-02-3 ]
[ 273404-37-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: sodium hydrogencarbonate / water / 21 h / 0 - 20 °C 2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane; N,N-dimethyl-formamide / 5.17 h / 0 - 20 °C 3: 10% Pd/C; hydrogen / methanol; ethyl acetate / 18 h 4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 18.67 h / 0 - 20 °C 5: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere 6: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 18.17 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: VERTEX PHARMACEUTICALS (OLD) - US9487555, 2016, B2

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H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 273404-37-8 ] {[proInfo.proName]}

Quality Control of [ 273404-37-8 ]

Related Doc. of [ 273404-37-8 ]

Product Details of [ 273404-37-8 ]

Calculated chemistry of [ 273404-37-8 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 273404-37-8 ]

Application In Synthesis of [ 273404-37-8 ]

[ 273404-37-8 ] Synthesis Path-Downstream 1~10

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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