[ CAS No. 139756-04-0 ]

Name: 139756-04-0|1-Methyl-4-(2-propoxybenzamido)-3-propyl-1H-pyrazole-5-carboxamide|97%
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Quality Control of [ 139756-04-0 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 139756-04-0 ]

CAS No. :	139756-04-0	MDL No. :	MFCD20270864
Formula :	C₁₈H₂₄N₄O₃	Boiling Point :	457.8°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	344.41 g/mol	Pubchem ID :	11393797
Synonyms :

Calculated chemistry of of [ 139756-04-0 ]

Physicochemical Properties

Num. heavy atoms :	25
Num. arom. heavy atoms :	11
Fraction Csp3 :	0.39
Num. rotatable bonds :	9
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	96.48
TPSA :	99.24 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.36 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.84
Log Po/w (XLOGP3) :	2.88
Log Po/w (WLOGP) :	2.32
Log Po/w (MLOGP) :	1.41
Log Po/w (SILICOS-IT) :	2.32
Consensus Log Po/w :	2.36

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.52
Solubility :	0.104 mg/ml ; 0.000301 mol/l
Class :	Soluble
Log S (Ali) :	-4.62
Solubility :	0.00819 mg/ml ; 0.0000238 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.0
Solubility :	0.00342 mg/ml ; 0.00000993 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.12

Safety of [ 139756-04-0 ]

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 [ 139756-04-0 ]

* 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 [ 139756-04-0 ]
Downstream synthetic route of [ 139756-04-0 ]

[ 139756-04-0 ] Synthesis Path-Upstream 1~4

1
[ 2100-31-4 ]
[ 139756-02-8 ]
[ 139756-04-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: With thionyl chloride In dichloromethane for 3 h; Heating / reflux Stage #2: With dmap; triethylamine In dichloromethane at 0℃; for 1 h;	Step 8 2-Methyl-4-(2-propoxybenzoylamino)-5-propyl-2H-pyrazole-3-carboxamide: A solution of 2-propoxybenzoic acid (13.7 g, 76.1 mmol) and thionyl chloride (36.2 g, 304.4 mmol) in dry dichloromethane (80 mL) was heated for 3 hours at reflux. The solvent and excess thionyl chloride were distilled off under reduced pressure. The residue was taken up in dry dichloromethane (60 mL) and reacted with a solution of 4-amino-2-methyl-5-propyl-2H-pyrazole-3-carboxamide (12.6 g, 69.2 mmol), dry triethylamine (7 g, 69.2 mmol) and 4-(N,N-dimethylamino)pyridine (84.5 mg, 0.7 mmol) in dry dichloromethane (200 mL) at 0° C. Stirring was maintained for 1 hour, and the reaction mixture was successively washed with water (150 mL), saturated aqueous sodium carbonate solution (200 mL) and saturated brine (200 mL). The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated to about 60 mL, and then hexane (150 mL) was added to give precipitate product as a white solid (22 g, 92percent). ¹H NMR (300 MHz, CDCl₃) δ 9.47 (s, 1H), 8.28 (d, 1H, J=7.8 Hz), 7.87 (br.s, 1H), 7.57-7.52 (m, 1H), 7.16-7.05 (m, 2H), 5.53 (s, 1H), 4.20 (t, 2H, J=6.6 Hz), 4.09 (s, 3H), 2.54 (t, 2H, J=7.5 Hz), 1.97-1.85 (m, 2H), 1.69-1.26 (m, 2H), 1.07 (t, 3H, J=7.2 Hz), 0.95 (t, 3H, J=7.5 Hz). LC-MS: m/z=345 (M+H)⁺

Reference： [1] Patent: US2008/194529, 2008, A1, . Location in patent: Page/Page column 57-58
[2] Patent: US2003/176696, 2003, A1,

2
[ 54090-36-7 ]
[ 139756-02-8 ]
[ 139756-04-0 ]

Reference： [1] Patent: CN103755709, 2016, B, . Location in patent: Paragraph 0072

3
[ 54090-36-7 ]
[ 139756-04-0 ]

Reference： [1] Patent: US5250534, 1993, A,
[2] Patent: US6200980, 2001, B1,

4
[ 54090-36-7 ]
[ 139756-03-9 ]
[ 139756-04-0 ]

Reference： [1] Patent: US5272147, 1993, A,
[2] Patent: US6200980, 2001, B1,

[ 139756-04-0 ] Synthesis Path-Downstream 1~32

1
[ 139756-04-0 ]
[ 361340-56-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 1895 - 1899

2
[ 139756-04-0 ]
[ 374776-34-8 ]

Yield	Reaction Conditions	Operation in experiment
31%	With chlorosulfonic acid; at 0 - 20℃; for 2h;	Step 9 3-(5-Carbamoyl-1-methyl-3-propyl-1H-pyrazol-4-ylcarbamoyl)-4-propxy-benzenesulfonyl chloride: 2-Methyl-4-(2-propoxybenzoylamino)-5-propyl-2H-pyrazole-3-carboxamide (20 g, 58.1 mmol) was added to chlorosulfonic acid (81.3 g, 698 mmol) at 0 C. and the reaction was warmed to ambient temperature and stirred for 2 hours. The reaction mixture was poured into ice water (800 g) and mechanically stirred for 1 hour to give a white solid, which was filtered and washed with water. Following standard extractive work up, the solvent was evaporated under reduced pressure to yield the title compound (8 g, 31%). 1H NMR (300 MHz, CDCl3) delta 9.19 (s, 1H), 8.97 (s, 1H), 8.19 (t, 1H, J=8.9 Hz), 7.56 (br. s, 1H), 4.35 (t, 2H, J=6.6 Hz), 4.07 (s, 3H), 2.53 (t, 2H, J=7.5 Hz), 2.06-1.94 (m, 2H), 1.78-1.60 (m, 2H), 1.18 (t, 3H, J=7.5 Hz), 0.95 (t, 3H, J=7.2 Hz); LC-MS: m/z=443.1 (M+H)+
	In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ethyl acetate;	(Step a) Preparation of 4-[2-Propoxy-5-(Chlorosulfonyl)Benzamido]-1-Methyl-3-Propyl-5-Carbamoyl Pyrazole To 23 ml of chlorosulfonic acid cooled to 0 C., 10 g of <strong>[139756-04-0]4-[2-propoxy benzamido]-1-methyl-3-propyl-5-carbamoyl pyrazole</strong> was added and then stirred at room temperature for 2 hours. Reaction mixture was added to ice water of 0 C. and then stirred for 1 hour to obtain white solid, which was filtered and washed with water. The obtained white solid was dissolved in ethyl acetate. The solution was successively washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain a crude product and triturated with hexane to give 9.14 g of the title compound. 1H NMR (CDCl3): 0.92(t,3H), 1.08(t,3H), 1.62(m,2H), 1.97(m,2H), 2.50(t, 2H), 4.04(s,3H), 4.32(t,2H), 5.63(br s,1H), 7.24(d,1H), 7.54(br s, 1H), 8.15(dd,1H), 8.93(d,1H), 9.17(br s,1H)
	With thionyl chloride; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; hexane; ethyl acetate;	(Step 1) Preparation of 4-[2-Propoxy-5-(Chlorosulfonyl)Benzamido]-1-Methyl-3-Propyl-5-Carbamoyl Pyrazole To 32.8 ml of chlorosulfonic acid cooled to 0 C., 8.48 ml of thionyl chloride and 20 g of <strong>[139756-04-0]4-[2-propoxy benzamido]-1-methyl-3-propyl-5-carbamoyl pyrazole</strong> were successively added dropwise and portionwise, and then stirred for 2 hours at room temperature. Reaction mixture was added to ice water of 0 C. After 1 hour, the reaction mixture was extracted with ethyl acetate. The organic solution was successively washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain a crude product and triturated with a mixture of hexane:ethyl acetate (10:1) to give 23 g of the title compound. 1H NMR(CDCl3): 0.92(t,3H), 1.08(t,3H), 1.62(m,2H), 1.97(m,2H), 2.50(t, 2H), 4.04(s,3H), 4.32(t,2H), 5.63(br s,1H), 7.24(d,1H), 7.54(br s, 1H), 8.15(dd,1H), 8.93(d,1H), 9.17(br s,1H).

With chlorosulfonic acid; at 0℃;

In step 1, 4-[2-propyloxy-5-(chlorosulfonyl)benzamido] - l-methyl-3-propyl-5-carbamoyl pyrazole is prepared. Precisely, the proper amount of 4-[2-propyloxy benzamido]-l-methyl-3-propyl-5-carbamoyl pyrazole is added to the solution of the proper amount of chlorosulfonic acid cooled at 0 0C. The mixture is stirred, filtered, washed and dried to give 4-[2-propyloxy-5-(chlorosulfonyl)benzamido ]- l-methyl-3-propyl-5-carbamoyl pyrazole.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 3013 - 3021
[2]Patent: US2008/194529,2008,A1 .Location in patent: Page/Page column 58
[3]Patent: US2003/176696,2003,A1
[4]Patent: US2003/176696,2003,A1
[5]Patent: WO2006/132460,2006,A1 .Location in patent: Page/Page column 7

3
[ 139756-04-0 ]
5-(5-(4-(hydroxycarbonyl)piperidinylsulfonyl)-2-n-propoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one [ No CAS ]