[ CAS No. 1380087-89-7 ] {[proInfo.proName]}

Name: 1380087-89-7|(S)-2-(6-(4-Chlorophenyl)-1-methyl-4H-benzo[c]isoxazolo[4,5-e]azepin-4-yl)acetamide|98%
Brand: Ambeed
SKU: A137689
Rating: 99 (28 reviews)

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2D 3D

Structure of 1380087-89-7 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 1380087-89-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1380087-89-7 ]

SDS Specification

Alternatived Products of [ 1380087-89-7 ]

Product Details of [ 1380087-89-7 ]

CAS No. :	1380087-89-7	MDL No. :	MFCD28144505
Formula :	C₂₀H₁₆ClN₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GCWIQUVXWZWCLE-INIZCTEOSA-N
M.W :	365.81	Pubchem ID :	57389999
Synonyms :	CPI-0610

Calculated chemistry of [ 1380087-89-7 ]

Physicochemical Properties

Num. heavy atoms :	26
Num. arom. heavy atoms :	17
Fraction Csp3 :	0.15
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	103.75
TPSA :	81.48 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.39 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.9
Log Po/w (XLOGP3) :	3.02
Log Po/w (WLOGP) :	3.37
Log Po/w (MLOGP) :	2.27
Log Po/w (SILICOS-IT) :	4.77
Consensus Log Po/w :	3.27

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.3
Solubility :	0.0185 mg/ml ; 0.0000505 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.4
Solubility :	0.0147 mg/ml ; 0.0000402 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-7.57
Solubility :	0.00000976 mg/ml ; 0.0000000267 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	4.22

Safety of [ 1380087-89-7 ]

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 [ 1380087-89-7 ]

* 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 [ 1380087-89-7 ]

[ 1380087-89-7 ] Synthesis Path-Downstream 1~8

1
[ CAS Unavailable ]
[ 1380087-89-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: hydrogenchloride / methanol; 1,4-dioxane / 1 h / 20 °C 2: isopropylmagnesium bromide / tetrahydrofuran / 0.5 h / -30 - -5 °C 3: dmap / tetrahydrofuran / 0.5 h / 20 °C 4: tetrahydrofuran / -30 - 20 °C 5: trifluoroacetic acid / chloroform / 24 h / Reflux 6: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 2 h / 20 °C 7: ammonia / dichloromethane; tetrahydrofuran / 1 h / -30 °C

Reference： [1]Albrecht, Brian K.; Gehling, Victor S.; Hewitt, Michael C.; Vaswani, Rishi G.; Côté, Alexandre; Leblanc, Yves; Nasveschuk, Christopher G.; Bellon, Steve; Bergeron, Louise; Campbell, Robert; Cantone, Nico; Cooper, Michael R.; Cummings, Richard T.; Jayaram, Hariharan; Joshi, Shivangi; Mertz, Jennifer A.; Neiss, Adrianne; Normant, Emmanuel; O'Meara, Michael; Pardo, Eneida; Poy, Florence; Sandy, Peter; Supko, Jeffrey; Sims, Robert J.; Harmange, Jean-Christophe; Taylor, Alexander M.; Audia, James E. [Journal of Medicinal Chemistry, 2016, vol. 59, # 4, p. 1330 - 1339]

2
[ CAS Unavailable ]
[ 1380087-89-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: isopropylmagnesium bromide / tetrahydrofuran / 0.5 h / -30 - -5 °C 2: dmap / tetrahydrofuran / 0.5 h / 20 °C 3: tetrahydrofuran / -30 - 20 °C 4: trifluoroacetic acid / chloroform / 24 h / Reflux 5: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 2 h / 20 °C 6: ammonia / dichloromethane; tetrahydrofuran / 1 h / -30 °C

3
[ 1380089-99-5 ]
[ 1380087-89-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: dmap / tetrahydrofuran / 0.5 h / 20 °C 2: tetrahydrofuran / -30 - 20 °C 3: trifluoroacetic acid / chloroform / 24 h / Reflux 4: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 2 h / 20 °C 5: ammonia / dichloromethane; tetrahydrofuran / 1 h / -30 °C

4
[ 2086298-56-6 ]
[ 1380087-89-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: tetrahydrofuran / -30 - 20 °C 2: trifluoroacetic acid / chloroform / 24 h / Reflux 3: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 2 h / 20 °C 4: ammonia / dichloromethane; tetrahydrofuran / 1 h / -30 °C

5
[ 2086298-57-7 ]
[ 1380087-89-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: trifluoroacetic acid / chloroform / 24 h / Reflux 2: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 2 h / 20 °C 3: ammonia / dichloromethane; tetrahydrofuran / 1 h / -30 °C

6
[ 1380089-81-5 ]
[ 1380087-89-7 ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: 2-[(7S)-9-(4-chlorophenyl)-3-methyl-5-oxa-4,8-diazatricyclo[8.4.0.0²,⁶]tetradeca-1⁽¹⁰⁾,2⁽⁶⁾,3,8,11,13-hexaen-7-yl]acetic acid With 1,1'-carbonyldiimidazole In dichloromethane at 15 - 25℃; Stage #2: With ammonium hydroxide In dichloromethane at 0 - 5℃; for 1.33333h;	To produce crystalline material, a reactor was charged with 700 g of carboxylic acid (1) with 65.8 wt 1H NMR potency (460 g, 1.3 mol) in DCM (4.6 L). The batch was charged with carbonyldiimidazole (CDI, 264 g, 1.6 mol, 1.3 equiv) in four portions with the solids addition system. Over the course of the addition, the batch temperature was 15-18 °C. The batch was stirred for 1-2 hours at 20-25 °C when HPLC analysis indicated the starting material was <2%. The batch was cooled to 0-5 °C. The batch was charged with 28% aqueous ammonium hydroxide solution (432 mL, 6.5 mol, 5 equiv) by an addition funnel over 20 minutes while maintaining the temperature at 0-5 °C. The batch was stirred at 0-5 °C for 1 hour when HPLC analysis indicated the intermediate acyl-imidazole was <2%. The batch was warmed to 20-25 °C and DI water (2.3 L) was added. The batch was stirred vigorously for 15 minutes. The stirring was stopped and the phases were separated. The organic phase was washed with brine (2.3 L), dried (MgS04), treated with activated carbon (46 g, Darco G-60), filtered, and washed with DCM (1.5 L). The combined filtrates and washes were concentrated to dryness by rotary evaporation. The residue was redissolved in absolute alcohol (2.3 L) and heated to 50-55 °C. The batch was charged with DI water (2.3 L) by addition funnel over 1 hour while maintaining the temperature 50-55 °C. The batch was cooled over a period of 2 hours and an oil, instead of solids, was observed to form. The batch was reheated to 50-55 °C and gradually cooled to 15-25 °C over a period of 12-16 hours. The batch was cooled to 0-5 °C and stirred for 1-2 hours. The batch was filtered and washed with a 1: 1 mixture of DI water to absolute ethanol (230 mL). [0068] The solids were dried under high vacuum at 40-45 °C overnight to afford monohydrate crystalline Form A of 2-((4S)-6-(4-chlorophenyl)-l-methyl-4H- benzo[c]isoxazolo[4,5-e]azepin-4-yl)acetamide [320 g, 70% yield, 95.1% (AUC) by HPLC]. Robertson Microlit analyzed the palladium level to be 84 ppm. XRPD, NMR, TGA, DSC, and an optical micrograph are depicted in Figures 1-3 and 5. Karl Fisher analysis confirmed an average water content of 4.5 wt%. The listing of XRPD peaks shown in Figure 1 are provided in Table 1 below.
	Multi-step reaction with 2 steps 1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 2 h / 20 °C 2: ammonia / dichloromethane; tetrahydrofuran / 1 h / -30 °C

Reference： [1]Current Patent Assignee: MORPHOSYS AG - WO2015/195862, 2015, A1 Location in patent: Paragraph 0067-0068
[2]Albrecht, Brian K.; Gehling, Victor S.; Hewitt, Michael C.; Vaswani, Rishi G.; Côté, Alexandre; Leblanc, Yves; Nasveschuk, Christopher G.; Bellon, Steve; Bergeron, Louise; Campbell, Robert; Cantone, Nico; Cooper, Michael R.; Cummings, Richard T.; Jayaram, Hariharan; Joshi, Shivangi; Mertz, Jennifer A.; Neiss, Adrianne; Normant, Emmanuel; O'Meara, Michael; Pardo, Eneida; Poy, Florence; Sandy, Peter; Supko, Jeffrey; Sims, Robert J.; Harmange, Jean-Christophe; Taylor, Alexander M.; Audia, James E. [Journal of Medicinal Chemistry, 2016, vol. 59, # 4, p. 1330 - 1339]

7
[ CAS Unavailable ]
[ 1380087-89-7 ]

Yield	Reaction Conditions	Operation in experiment
40.2 g	With ammonia In tetrahydrofuran; dichloromethane at -30℃; for 1h;

8
[ CAS Unavailable ]
[ 1380087-89-7 ]

Yield	Reaction Conditions	Operation in experiment
320 g	With water In ethanol at 50 - 55℃; for 1h;	Preparation of monohydrate 2-((4S)-6-(4-chlorophenyl)-l-methyl-4H- benzo[c]isoxazolo[4,5-e]azepin-4-yl)acetamide The residue was redissolved in absolute alcohol (2.3 L) and heated to 50- 55 °C. The batch was charged with DI water (2.3 L) by addition funnel over 1 hour while maintaining the temperature 50-55 °C. The batch was cooled over a period of 2 hours and an oil, instead of solids, was observed to form. The batch was reheated to 50-55 °C and gradually cooled to 15-25 °C over a period of 12-16 hours. The batch was cooled to 0-5 °C and stirred for 1-2 hours. The batch was filtered and washed with a 1 : 1 mixture of DI water to absolute ethanol (230 mL). The solids were dried under high vacuum at 40-45 °C overnight to afford monohydrate 2-((4S)-6-(4-chlorophenyl)-l-methyl-4H-benzo[c]isoxazolo[4,5-e]azepin-4- yl)acetamide [320 g, 70% yield, 95.1% (AUC) by HPLC, m/z 366 [M+H]+]. Karl Fisher analysis confirmed an average water content of 4.5 wt%. As shown by Figure 6, optical microscopy confirmed the monohydrate to be crystalline.

Reference： [1]Current Patent Assignee: MORPHOSYS AG - WO2015/195863, 2015, A1 Location in patent: Paragraph 0047; 0048

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[ CAS No. 1380087-89-7 ] {[proInfo.proName]}

Quality Control of [ 1380087-89-7 ]

Related Doc. of [ 1380087-89-7 ]

Product Details of [ 1380087-89-7 ]

Calculated chemistry of [ 1380087-89-7 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1380087-89-7 ]

Application In Synthesis of [ 1380087-89-7 ]

[ 1380087-89-7 ] Synthesis Path-Downstream 1~8

Precautionary Statements-General

Prevention

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