[ CAS No. 1057652-23-9 ]

Name: 1057652-23-9|Methyl 4-amino-3-cyclopropylbenzoate|98%
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Quality Control of [ 1057652-23-9 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 1057652-23-9 ]

CAS No. :	1057652-23-9	MDL No. :	MFCD27938576
Formula :	C₁₁H₁₃NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	191.23 g/mol	Pubchem ID :	-
Synonyms :

Calculated chemistry of of [ 1057652-23-9 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.36
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	54.59
TPSA :	52.32 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) :	-6.05 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.22
Log Po/w (XLOGP3) :	2.0
Log Po/w (WLOGP) :	1.88
Log Po/w (MLOGP) :	1.84
Log Po/w (SILICOS-IT) :	2.02
Consensus Log Po/w :	1.99

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.4
Solubility :	0.753 mg/ml ; 0.00394 mol/l
Class :	Soluble
Log S (Ali) :	-2.73
Solubility :	0.36 mg/ml ; 0.00188 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.72
Solubility :	0.367 mg/ml ; 0.00192 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.6

Safety of [ 1057652-23-9 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1057652-23-9 ]

* 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 [ 1057652-23-9 ]

[ 1057652-23-9 ] Synthesis Path-Downstream 1~11

1
[ 1057652-23-9 ]
[ 2191433-08-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: acetic acid / 0.5 h / 5 - 10 °C 1.2: 0 - 30 °C 2.1: copper(ll) bromide; tert.-butylnitrite / acetonitrile / 12 h / 30 °C
	Multi-step reaction with 2 steps 1: acetic acid; bromine / 0 - 30 °C 2: copper(ll) bromide; tert.-butylnitrite / acetonitrile / 12 h / 30 °C
	Multi-step reaction with 2 steps 1: bromine; acetic acid / water / 2 h / 0 - 20 °C 2: isopentyl nitrite; copper(I) bromide / acetonitrile / 1 h / 20 °C / Inert atmosphere; Cooling with ice

Reference： [1]Current Patent Assignee: ARDELYX, INC. - WO2018/39386, 2018, A1
[2]Current Patent Assignee: ARDELYX, INC. - WO2018/39384, 2018, A1
[3]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2020/234333, 2020, A1

2
[ 1057652-23-9 ]
[ CAS Unavailable ]
[ 2191433-07-3 ]

Yield	Reaction Conditions	Operation in experiment
55%	With bromine; acetic acid In water at 0 - 20℃; for 2h;	B.10.10.1 Methyl 2-amino-4-cyclopropylbenzo[d]thiazole-6-carboxylate To a mixture of sodium thiocyanate (1.3 g, 16 mmol) in HOAc (15 mL) at 0°C was added dropwise a solution of intermediate N1 (0.77 g, 4.0 mmol) in HOAc (15 mL) followed by the addition of Bromine (0.25 mL, 4.83 mmol) dropwise. The reaction mixture was stirred at rt for overnight. Water (50 mL) was added and stirred at rt for 2 h. The yellow precipitate was filtered. The solid obtained was diluted in DCM/MeOH (9/1) and basified with NH3aq until pH 8. The resulting mixture was filtered through a short pad of Celite. The organic layer was evaporated till dryness and the residue was taken up in MeOH and stirred overnight at rt. The solid was filtered and rinsed with MeOH and dried in vacuo to give intermediate N2 (0.55 g, 55%) as a yellow solid.
	Stage #1: methyl 4-amino-3-cyclopropylbenzoate; sodium thiocyanide With acetic acid at 5 - 10℃; for 0.5h; Stage #2: With bromine at 0 - 30℃;	11.2 Step 2. Methyl2-amino-4-cyclopropyl-1,3-benzothiazole-6-carboxylate (A-7c) To a 500 mL round-bottom flask containing methyl4-amino-3-cydopropylbenzoateA-7b (16 g, 83.67 mmol, 1.0 equiv.) and AcOH (200 mL) was added sodium thiocyanate(27.13 g, 334.64 mmol, 4.0 equiv.) and the resulting mixture wa.s stirred for 0.5 hat 5-10 °C.A solution of bromine (13 3 g, 83.22 mmoL 0.99 equiv.) in AcOH (1 00 mL) was then added20 drop'.vise with at 0-5 °C and the resulting mixture '.vas stirred at 0-5°C for 10 min and then at30 °C overnight. 1500 mL ofi-hO was then added and the pH of the aqueous solution wasadjusted to 8-9 using potassium carbonate. The resulting solids were collected by filtrationand dried in an oven under reduced pressure to afford 24 g (crude) ofmethyl2-amino-4-cyclopropyl-1 ,3-benzothiazole-6-carboxylate A-7c as an orange colored solid. The crude25 product was carried onto the next step without further purification.
	With bromine; acetic acid at 0 - 30℃;	7.2 Step 2, Methyl 2-amino-4-cyclopropyl-l,3-benzothiazole-6-carboxylate (A-7c) To a 500 mL round-bottom flask was added methyl 4-amino-3-cyclopropylbenzoate A- 7b (16 g, 83.67 mmol, 1.0 equiv.), AcOH (200 mL) and NaSCN (27.13 g, 334.64 mmol, 4.0 equiv.), and the resulting mixture was stirred for 0.5 h at 5-10 °C, A solution of bromine (13,3 g, 83.22 mmol, 0.99 equiv.) in AcOH (100 mL) was then added dropwise at 0-5 °C and the resulting mixture was stirred at 0-5 °C for 10 min, then at 30 °C overnight. H2O was added (1500 mL) and the pH of the solution was adjusted to 8-9 using potassium carbonate. The resulting solids were collected by filtration and dried in an oven under reduced pressure to afford methyl 2-amino-4-cyclopropyl-l,3-benzothiazole-6-carboxylate A-7c (24 g) as an orange solid. The product was carried on to the next step without further purification.

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2020/234333, 2020, A1 Location in patent: Page/Page column 16; 83-84
[2]Current Patent Assignee: ARDELYX, INC. - WO2018/39386, 2018, A1 Location in patent: Page/Page column 135
[3]Current Patent Assignee: ARDELYX, INC. - WO2018/39384, 2018, A1 Location in patent: Paragraph 00341

3
[ 106896-49-5 ]
[ 411235-57-9 ]
[ 1057652-23-9 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium phosphate; palladium diacetate; tricyclohexylphosphine In toluene at 100℃; Inert atmosphere;	11.1 Step j Methyl4-amino-3-cyclopropylbenzoate (A-7b) To a 1000 mL round-bottom flask, purged and maintained under an inert atmosphereofnitrogen, was added methyl4-amino-3-bromobenzoate A-7a (25 g, 108.67 mmol, 1.0equiv.), K3P0c~ (65 g, 306.21 mmol, 2.82 equiv.), toluene (50 mL), water (100 mL), P(Cy)3(2 8 g, 0.05 equiv.), Pd(OAc)2 (2.2.5 g, 10.02 mmol, ).09 equiv.), and cyclopropyl boronicacid (26 g, 302.69 mmol, 2.79 equiv.) and the resulting mixture was heated at 100 °C10 overnight. The resulting solids were filtered off and the filtrate vvas diluted ·with 200 mL ofH20 and extracted with ethyl acetate (200 mL x 3). The combined organic layers wereconcentrated in vacuo and the resulting residue Vas purified by silica gel columnchromatography eluting with ethyl acetate/petroleum ether (1 :20 to 1.10 a.nd then to 1 :5) toprovide19.9 g (96%) of methyl 4-amino-3-cyclopropylbenzoate A-7b a.s a light brown solid.
96%	With potassium phosphate; palladium diacetate; tricyclohexylphosphine In water; toluene at 100℃; Inert atmosphere;	7.1 Step 1. Methyl 4-amino-3-cyciopropylbenzoate (A-7b) To a 1 L round-bottom flask, purged and maintained under an inert atmosphere of nitrogen, was added methyl 4-amino-3-bromobenzoate A-7a (25 g, 108.67 mmol , 1.0 equiv.), K3PO4 (65 g, 306.21 mmol, 2.82 equiv.), toluene (50 mL), water (100 mL), P(Cy)s (2.8 g, 0.05 equiv.), Pd(OAc)2 (2.25 g, 10.02 mmol, 0.09 equiv.), and cyclopropyl boronic acid (26 g, 302.69 mmol, 2.79 equiv.). The resulting mixture was heated at 100 °C overnight. The resulting solids were removed by filtration. The filtrate was diluted with H2O (200 mL) and extracted with ethyl acetate (200 mL x 3). The combined organic layers were concentrated in vacuo and the resulting residue was purified via silica gel column chromatography eluting with EtOAc PE (1 :20 to 1 : 10 and to 1 :5) to provide methyl 4-amino-3-cyclopropylbenzoate A-7b (19.9 g, 96%) as a light brown solid.
96%	With palladium diacetate; tricyclohexylphosphine In water; toluene at 100℃; for 4h; Inert atmosphere;	41 Palladium acetate (48.8mg, 0.217mmol), tris(cyclohexyl)phosphine (61.0mg, 0.217mmol) and potassium phosphate (1.38g, 6.52mmol) were added to toluene (10mL) with compound 41a (500mg, 2.17mmol) dissolved )/Water (2mL) mixed solution.The resulting reaction solution was stirred for 4 hours under nitrogen protection and 100°C.The reaction solution was cooled and filtered through Celite. The crude product obtained by concentrating the filtrate under reduced pressure was purified by column chromatography (petroleum ether/ethyl acetate = 2/1) to obtain compound 41b as a yellow solid(400mg, 96% yield).

93%

With potassium phosphate; tricyclohexylphosphine In water; toluene at 120℃; for 0.75h; Microwave irradiation;

B.10.10.1 Methyl 4-amino-3-cyclopropylbenzoate To a solution of 4-amino-3-bromobenzoic acid methyl ester (1.0 g, 4.4 mmol) in toluene (15 mL), were added cyclopropylboronic acid (0.56 g, 6.5 mmol), K3PO4 (2.8 g, 13 mol), tricyclohexylphoshine (0.12 g, 0.44 mmol) and H2O (2 mL). The reaction mixture was purged again for 2 min then was heated at 120°C using a single mode microwave (Anton Paar Monowave 300) with a power output ranging from 0 to 850 W for 45 min. The reaction mixture was filtered through a pad of Celite and washed with EtOAc and H2O. The filtrate obtained was extracted with EtOAc and the organic layer was washed with brine, dried over MgSO4, filtered and evaporated till dryness. The residue was purified by preparative LC (regular SiOH 30 µm, 40 g Interchim, mobile phase gradient: from heptane / EtOAc from 100:0 to 70:30). The pure fractions were combined and evaporated under vacuum to give intermediate N1 as a yellow oil (0.77 g, 93%).

Reference： [1]Current Patent Assignee: ARDELYX, INC. - WO2018/39386, 2018, A1 Location in patent: Page/Page column 135
[2]Current Patent Assignee: ARDELYX, INC. - WO2018/39384, 2018, A1 Location in patent: Paragraph 00340
[3]Current Patent Assignee: XIAMEN BIOTIME BIOTECHNOLOGY - CN112028891, 2020, A Location in patent: Paragraph 0344-0346
[4]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2020/234333, 2020, A1 Location in patent: Page/Page column 16; 83-84

4
[ 1065010-87-8 ]
[ 106896-49-5 ]
methyl 4-amino-3-cyclopropylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium phosphate; palladium diacetate; ruphos In water; toluene at 110℃; for 2.5h; Inert atmosphere;	4 Example 4: compound (115) in Table I According to procedure (J), a solution of methyl 4-amino-3-bromobenzoate (3.00 g, 12.8 mmoles, 1 eq.) and potassium cyclopropyltrifluoroborate (2.84 g, 19.2 mmoles, 1.5 eq.) in toluene (52.5 mL) and water (13.5 mL) was degassed with argon during 5 minutes then tripotassium phosphate (6.88 g, 31.9 mmoles, 2.5 eq.), RuPhos (239 mg, 511 pmoles, 0.04 eq.) and palladium(II) acetate (57.9 mg, 256 pmoles, 0.02 eq.) were added. The reaction mixture was heated at H0°C and stirred for 2h30 under inert atmosphere. Upon cooling down to room temperature, it was filtered over a pad of celite and the pad was washed with EtOAc. A saturated aqueous solution of brine was then added to the filtrate and the mixture was extracted with EtOAc. The combined organic layers were dried over MgS04, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel to give methyl 4-amino-3-cyclopropylbenzoate (2.02 g, 81 %).H1 NMR (400 MHz, d6-DMSO) δ7.53 (dd, J = 8.4, 2.0 Hz, 1H), 7.42 (d, J = 1.9 Hz, 1H), 6.63 (d, J = 8.4 Hz, 1H), 5.87 (s, 2H), 3.73 (s, 3H), 1.65 (tt, J = 8.3, 5.4 Hz, 1H), 0.95 - 0.82 (m, 2H), 0.54 - 0.40 (m, 2H).
81%	With potassium phosphate; palladium diacetate; ruphos In water; toluene at 110℃; for 2.5h; Inert atmosphere;	4 Example 4: compound (41) in Table I According to procedure (E), a solution of methyl 4-amino-3-bromobenzoate (3.00 g, 12.8 mmoles, 1 eq.) and potassium cyclopropyltrifluoroborate (2.84 g, 19.2 mmoles, 1.5 eq.) in toluene (52.5 mL) and water (13.5 mL) was degassed with argon during 5 minutes then tripotassium phosphate (6.88 g, 31.9 mmoles, 2.5 eq.), RuPhos (239 mg, 511 pmoles, 0.04 eq.) and palladium(II) acetate (57.9 mg, 256 pmoles, 0.02 eq.) were added. The reaction mixture was heated at 110°C and stirred for 2h30 under inert atmosphere. Upon cooling down to room temperature, it was filtered over a pad of celite and the pad was washed with EtOAc. A saturated aqueous solution of brine was then added to the filtrate and the mixture was extracted with EtOAc. The combined organic layers were dried over MgSO-u filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel to give methyl 4-amino-3-cyclopropylbenzoate (2.02 g, 81 %). NMR (400 MHz, ifc-DMSO) d 7.53 (dd, J = 8.4, 2.0 Hz, 1H), 7.42 (d, J = 1.9 Hz, 1H), 6.63 (d, J = 8.4 Hz, 1H), 5.87 (s, 2H), 3.73 (s, 3H), 1.65 (tt, J= 8.3, 5.4 Hz, 1H), 0.95 - 0.82 (m, 2H), 0.54 - 0.40 (m, 2H).

Reference： [1]Current Patent Assignee: UNIVERSITY OF MONTPELLIER; ABIVAX SA; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; INSTITUT CURIE - WO2020/11811, 2020, A1 Location in patent: Page/Page column 57
[2]Current Patent Assignee: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITY OF MONTPELLIER; ABIVAX SA; INSTITUT CURIE - WO2021/13733, 2021, A1 Location in patent: Page/Page column 101

5
[ 1057652-23-9 ]
[ 2408728-99-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: caesium carbonate; [(2-di-cyclohexylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1‘-biphenyl)-2-(2‘-amino-1,1’-biphenyl)]palladium(II) methanesulfonate / N,N-dimethyl-formamide / 1.25 h / 80 °C / Inert atmosphere 2: water; sodium hydroxide / methanol / 3 h / 80 °C
	Multi-step reaction with 2 steps 1: [(2-di-cyclohexylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1‘-biphenyl)-2-(2‘-amino-1,1’-biphenyl)]palladium(II) methanesulfonate; caesium carbonate / N,N-dimethyl-formamide / 1.25 h / 80 °C / Inert atmosphere 2: methanol; water; sodium hydroxide / 3 h / 80 °C

Reference： [1]Current Patent Assignee: UNIVERSITY OF MONTPELLIER; INSTITUT CURIE; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; ABIVAX SA - WO2020/11811, 2020, A1
[2]Current Patent Assignee: INSTITUT CURIE; UNIVERSITY OF MONTPELLIER; ABIVAX SA; MONGOLIAN UNIV; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; CURIE RES INSTITUTE - WO2021/13733, 2021, A1

6
[ 1057652-23-9 ]
[ 2408728-89-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: caesium carbonate; [(2-di-cyclohexylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1‘-biphenyl)-2-(2‘-amino-1,1’-biphenyl)]palladium(II) methanesulfonate / N,N-dimethyl-formamide / 1.25 h / 80 °C / Inert atmosphere 2: water; sodium hydroxide / methanol / 3 h / 80 °C 3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C

Reference： [1]Current Patent Assignee: UNIVERSITY OF MONTPELLIER; INSTITUT CURIE; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; ABIVAX SA - WO2020/11811, 2020, A1

7
[ 1057652-23-9 ]
[ 2408728-97-0 ]
[ 2408728-98-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With [(2-di-cyclohexylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1‘-biphenyl)-2-(2‘-amino-1,1’-biphenyl)]palladium(II) methanesulfonate; caesium carbonate In N,N-dimethyl-formamide at 80℃; for 1.25h; Inert atmosphere;	4 According to procedure (A), a reaction mixture of l-bromo-3-(3- cyclohexylpropoxy)benzene (547 mg, 1.84 mmole, 1.1 eq.), methyl 4-amino-3-cyclopropyl- benzoate (320 mg, 1.67 mmol, 1 eq.), BrettPhos Pd G3 (31.9 mg, 33.5 pmol, 0.02 eq) and CS2CO3 (818 mg, 2.51 mmol, 1.5 eq.) in anhydrous DMF (8 mL) was degassed with argon and heated at 80°C for 75 minutes under inert atmosphere. The reaction mixture was then cooled down to room temperature, filtered over a pad of celite and the pad was washed with EtOAc. Brine was then added to the filtrate and the mixture was extracted with EtOAc. The combined organic layers were dried over MgS04, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel to give methyl 4-[3-(3-cyclohexylpropoxy)phenyl]amino}-3-cyclopropylbenzoate (1.35 g, 80 %).H1 NMR (400 MHz, d6-DMSO) δ7.82 (s, 1H), 7.66 (dd, J = 8.5, 2.0 Hz, 1H), 7.54 (d, J = 2.0 Hz, 1H), 7.24 - 7.14 (m, 2H), 6.76 (d, J = 7.9 Hz, 1H), 6.73 (t, J = 2.1 Hz, 1H), 6.56 (dd, J = 8.1 , 2.2 Hz, 1H), 3.92 (t, J = 6.5 Hz, 2H), 3.78 (s, 3H), 1.94 (ddd, J = 13.8, 8.3, 5.4 Hz, 1H), 1.75 - 1.58 (m, 7H), 1.35 - 1.08 (m, 6H), 1.04 - 0.94 (m, 2H), 0.88 (q, J = 10.0, 9.3 Hz, 2H), 0.65 - 0.56 (m, 2H).
80%	With [(2-di-cyclohexylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1‘-biphenyl)-2-(2‘-amino-1,1’-biphenyl)]palladium(II) methanesulfonate; caesium carbonate In N,N-dimethyl-formamide at 80℃; for 1.25h; Inert atmosphere;	4 According to procedure (Al), a reaction mixture of l-bromo-3-(3-cyclohexylpropoxy)benzene (547 mg, 1.84 mmole, 1.1 eq.), methyl 4-amino-3-cyclopropyl-benzoate (320 mg, 1.67 mmole, 1 eq.), BrettPhos Pd G3 (31.9 mg, 33.5 pmoles, 2 mol%) and CS2CO3 (818 mg, 2.51 mmoles, 1.5 eq.) in anhydrous DMF (8 mL) was degassed with N2 and heated at 80°C for 75 minutes under inert atmosphere. The reaction mixture was cooled down to room temperature, filtered over a pad of celite and the pad was washed with EtOAc. A saturated aqueous solution of brine was then added to the filtrate and the mixture was extracted with EtOAc. The combined organic phases were dried over MgSO-i, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel to give methyl 4- { [3 -(3 -cy cl ohexylpropoxy)phenyl] amino } -3 - cy cl opropy lb enzoate (1.35 g, 80%). NMR (400 MHz, e-DMSO) d 7.82 (s, 1H), 7.66 (dd, J = 8.5, 2.0 Hz, 1H), 7.54 (d, J = 2.0 Hz, 1H), 7.24 - 7.14 (m, 2H), 6.76 (d, J= 7.9 Hz, 1H), 6.73 (t, J= 2.1 Hz, 1H), 6.56 (dd, J= 8.1, 2.2 Hz, 1H), 3.92 (t, J= 6.5 Hz, 2H), 3.78 (s, 3H), 1.94 (ddd, J = 13.8, 8.3, 5.4 Hz, 1H), 1.75 - 1.58 (m, 7H), 1.35 - 1.08 (m, 6H), 1.04 - 0.94 (m, 2H), 0.88 (q, ,/ = 10.0, 9.3 Hz, 2H), 0.65 - 0.56 (m, 2H).

Reference： [1]Current Patent Assignee: UNIVERSITY OF MONTPELLIER; INSTITUT CURIE; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; ABIVAX SA - WO2020/11811, 2020, A1 Location in patent: Page/Page column 57-58
[2]Current Patent Assignee: INSTITUT CURIE; UNIVERSITY OF MONTPELLIER; ABIVAX SA; MONGOLIAN UNIV; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; CURIE RES INSTITUTE - WO2021/13733, 2021, A1 Location in patent: Page/Page column 101; 102

8
[ 1057652-23-9 ]
[ 2561548-77-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: bromine; acetic acid / water / 2 h / 0 - 20 °C 2: isopentyl nitrite; copper(I) bromide / acetonitrile / 1 h / 20 °C / Inert atmosphere; Cooling with ice 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate / tetrahydrofuran; water / Inert atmosphere; Microwave irradiation

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2020/234333, 2020, A1

9
[ 1057652-23-9 ]
[ 2561548-78-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: bromine; acetic acid / water / 2 h / 0 - 20 °C 2: isopentyl nitrite; copper(I) bromide / acetonitrile / 1 h / 20 °C / Inert atmosphere; Cooling with ice 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate / tetrahydrofuran; water / Inert atmosphere; Microwave irradiation 4: lithium hydroxide monohydrate / tetrahydrofuran; water / 5 h / Reflux

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2020/234333, 2020, A1

10
[ 1057652-23-9 ]
[ 2561547-75-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: bromine; acetic acid / water / 2 h / 0 - 20 °C 2: isopentyl nitrite; copper(I) bromide / acetonitrile / 1 h / 20 °C / Inert atmosphere; Cooling with ice 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate / tetrahydrofuran; water / Inert atmosphere; Microwave irradiation 4: lithium hydroxide monohydrate / tetrahydrofuran; water / 5 h / Reflux 5: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2020/234333, 2020, A1

11
[ 1057652-23-9 ]
[ 2567983-84-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine; dmap / tetrahydrofuran / 2 h / 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / Cooling with ice 3: phosphorus tribromide / diethyl ether / 1 h / Cooling with ice

Reference： [1]Current Patent Assignee: XIAMEN BIOTIME BIOTECHNOLOGY - CN112028891, 2020, A

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P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
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. 1057652-23-9 ]

Quality Control of [ 1057652-23-9 ]

Related Doc. of [ 1057652-23-9 ]

Product Details of [ 1057652-23-9 ]

Calculated chemistry of of [ 1057652-23-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1057652-23-9 ]

Application In Synthesis of [ 1057652-23-9 ]

[ 1057652-23-9 ] Synthesis Path-Downstream 1~11

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry