2895-21-8|N-Isopropyl-2-chloroacetamide| Ambeed

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Quality Control of [ 2895-21-8 ] Purity: 97% SDS Specification

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NMR

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Product Details of [ 2895-21-8 ]

CAS No. :	2895-21-8
Formula :	C₅H₁₀ClNO
M.W :	135.59
SMILES Code :	O=C(NC(C)C)CCl
MDL No. :	MFCD00068034
InChI Key :	GYPNJSBBOATUPK-UHFFFAOYSA-N
Pubchem ID :	76171

Safety of [ 2895-21-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Computational Chemistry of [ 2895-21-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	8
Num. arom. heavy atoms	0
Fraction Csp3	0.8
Num. rotatable bonds	3
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	33.95
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	29.1 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.41
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	0.96
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.75
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.87
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	0.82
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.96

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.09
Solubility	11.1 mg/ml ; 0.0818 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.16
Solubility	9.41 mg/ml ; 0.0694 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.69
Solubility	2.75 mg/ml ; 0.0203 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.45 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.19

Application In Synthesis of [ 2895-21-8 ]

* 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 [ 2895-21-8 ]

[ 2895-21-8 ] Synthesis Path-Downstream 1~35

1
[ 91011-95-9 ]
[ 2895-21-8 ]
[ 132624-06-7 ]

References: [1]Journal of Organic Chemistry,1961,vol. 26,p. 339 - 343.

2
[ 2895-21-8 ]
[ 3338-24-7 ]
[ 2275-18-5 ]

References: [1]Die Entwicklung neuer insektizider Phosphorsaeure-Ester,3.Aufl.<Weinheim 1963>S.132,.
[2]Patent: GB791824,1956, .

3
[ 75-31-0 ]
[ 79-04-9 ]
[ 2895-21-8 ]

Yield	Reaction Conditions	Operation in experiment
70.3%	With potassium carbonate; In dichloromethane; at 20℃;Cooling with ice;	Isopropylamine (236.4 mg, 4.0 mmol)Was dissolved in 4 mL of dichloromethane,Anhydrous potassium carbonate (663.4 mg, 4.8 mmol) was added,The reaction flask was placed in an ice bath,Chloroacetyl chloride (451.8 mg, 4.0 mmol) was slowly added via a dropping funnel,The reaction was stirred at room temperature overnight. After completion of the reaction, 10 mL of ice water was added to quench the reaction,Dichloromethane, the combined organic phase was washed with saturated brine,Dried over anhydrous magnesium sulfate and distilled under reduced pressure without further purification to give a white solid. Yield: 70.3%
	With potassium carbonate; In dichloromethane; at 20℃;Cooling with ice;	General procedure: To a magnetically stirred solution of substituted aniline 1 (50.0 mmol, 1.0 equiv) and K2CO3 (75.0 mmol, 1.5 equiv) in CH2Cl2 (100 mL), cooled in an ice bath, the chloroacetyl chloride (60.0 mmol, 1.2 equiv) was added dropwise. The reaction mixture was stirred at room temperature and monitored by TLC (Indine as streak reagent). After the completion of the reaction, the solvents were removed under vacuum and water (50 mL) was added into the residue. The mixture was then extracted with ethyl acetate (3 x 50 mL). The organic layers were combined, dried over anhydrous MgSO4, and evaporated under vacuum to give the crude product 2 without further purification.
6.3 g	In dichloromethane; at 0 - 20℃; for 2h;	To a solution of propan-2-amine (5.9 g, 0.1 mol) in DCM (500 mL) was added 2- chloroacetyl chloride (11.1 g, 0.1 mol) drop wise at 0 C. The mixture was stirred at room temperature for 2 hrs. Then the mixture was quenched with water. The organic phase was washed with saturated brine, dried with anhydrous Na2 SO4, filtered and concentrated in vacuum to give the product titel compound (6.30 g) as a light yellow oil. ?H NIVIR (400 MHz, DMSO-d6)oe 6.37 (b, 1H), 4.14-4.02 (m, 1H), 1.20 (d, J = 6.8 Hz, 6H).

6.3 g	In dichloromethane; at 0 - 20℃; for 2h;	[0094] To a solution of propan-2-amine (5.9 g, 0.1 mol) in DCM (500 rriL) was added 2- chloroacetyl chloride (11.1 g, 0.1 mol) drop wise at 0 C. The mixture was stirred at room temperature for 2 hrs. Then the mixture was quenched with water. The organic phase was washed with saturated brine, dried with anhydrous Na2S04, filtered and concentrated in vacuum to give the product title compound (6.30 g) as a light yellow oil. 1H NMR (400 MHz, DMSO-d6) 5 6.37 (b, 1H), 4.14-4.02 (m, 1H), 1.20 (d, J = 6.8 Hz, 6H).
	With potassium carbonate; In dichloromethane; at 20℃;Cooling with ice;	Isopropylamine (354.7 mg, 6.0 mmol),Potassium carbonate (995.1 mg, 7.2 mmol) was placed in 6 mL of dichloromethane solution,Ice bath,Chloroacetyl chloride (677.6 mg, 6.0 mmol) was slowly added dropwise to the above reaction flask,Room temperature overnight.After the reaction,Add the right amount of water,Extracted three times with methylene chloride,Combined with organic saturated saturated brine,Dried over anhydrous magnesium sulfate,Distillation under reduced pressure to give the crude product as an off-white solid.Yield: 69.9%
	With potassium carbonate; In dichloromethane; at 20℃;Cooling with ice;	General procedure: To a magnetically stirred solution of substituted aniline 1 (50.0 mmol, 1.0 equiv.) and K2CO3 (75.0 mmol, 1.5 equiv.) in CH2Cl2 (100 mL), cooled in an ice bath, the chloroacetyl chloride (60.0 mmol, 1.2 equiv.) was added dropwise slowly. The reaction mixture was stirred at room temperature and monitored by TLC (iodine as streak reagent). After the reaction was completed, the solvent was removed under vacuum and ice water (50 mL) was added into the residue. The mixture was then extracted with ethyl acetate (3 × 50 mL). The organic layers were combined, dried over anhydrous MgSO4, and evaporated under vacuum to give the crude product 2 without further purification.
		General procedure: Triethylamine (0.3643 g, 3.6 mmol) was added to a solution of the appropriate alkylamine or substituted benzylamine 5a-l (3 mmol) in dichloromethane (7.5 mL), and the reaction mixture was stirred for 5 min at room temperature, then 2-chloroacetyl chloride (0.3857 g, 3.6 mmol) was added dropwise to this reaction mixture at 0 C and stirred for 15 min at room temperature. After completion of the reaction, the solvent was evaporated under reduced pressure to afford 6a-l. KI (0.5976 g, 3.6 mmol) and CTAB (98.40 mg, 7.5% mmol) were added to a solution of the crude product 6a-l in acetone (30 mL) and maintained stirring at reflux for 2 h to afford 7al. K2CO3 (0.2073 g, 3 mmol) was added to a solution of scopoletin (0.3843 g, 2 mmol) in acetone (30 mL), and the reaction mixture was stirred at refluxed for 30 min. Then crude intermediates 7a-l were added into the mixture and maintained reflux for 8-12 h (the reaction progress was monitored by TLC with UV detection). After cooling the reaction and filtration, the solvent was evaporated under reduced pressure, and the residue was dissolved in ethyl acetate, washed with saturation sodium bicarbonate, and saturation salt solution successively, dried over anhydrous sodium sulfate, evaporated under reduced pressure to give the target crude products. The crude products were purified by column chromatography using petroleum ether/ethyl acetate from 6:1 to 2:1 as the gradient eluent system to yield the products 26-37.
440 mg	With triethylamine; In dichloromethane; at 20℃; for 5h;	TDI01271-1 (1.0 g, 16.95 mmol) was dissolved in anhydrous dichloromethane (20 mL), and triethylamine (1.88g, 18.64 mmol) and chloroacetyl chloride (2.1 g, 18.64 mmol) were slowly added dropwise. The reaction was performedat room temperature for 5 hours. LC-MS indicated the reaction was complete. The reaction solution was concentratedunder reduced pressure, and the crude product was extracted with saturated dichloromethane (150 mL), and washedwith saturated brine (100 mL). The organic phase was dried over anhydrous sodium sulfate, filtered, and concentratedto afford TDI01271-2 (440 mg, crude product).1H NMR (400 MHz, DMSO-d6) delta 8.13 (s, 1H), 3.99 (s, 2H), 3.87-3.79 (m, 1H), 1.07 (d, J = 6.4 Hz, 6H). MS m/z (ESI):136.2 [M+H].
	With potassium carbonate; In tetrahydrofuran; acetonitrile; at 0 - 20℃; for 3h;	General procedure: To a solution of 9 (30mmol) in 25mL THF was added K2CO3 (6.2g, 45mmol), and stirred for 20min under the ice bath to make it well mixed. Chloroacetyl chloride (3mL, 36mmol) was added in drops and stirred for 3h under room temperature. The reaction solution was concentrated, water (100mL) was added, and extracted with EtOAc. The organic layer was collected and washed with saturated salt solution for three times, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude material was purified by column chromatography to afford intermediate product 10.
	With triethylamine; In dichloromethane;Cooling with ice;	third step:Isopropylamine,Dichloromethane as a solvent,Add triethylamine (1 mmol),Chloroacetyl chloride (1 mmol) diluted slowly with dichloromethane in a constant pressure dropping funnel under ice conditions, after the reaction is completed, the system is poured into water, the pH is adjusted to weakly basic with Na2CO3, and dichloromethane extraction , The organic phase was concentrated under reduced pressure,The mixture was stirred, filtered, and dried with n-hexane to obtain 2-chloro-N-isopropylacetamide.
6.3 g	In dichloromethane; at 0 - 20℃; for 2h;	To a solution of propan-2-amine (5.9 g, 0.1 mol) in DCM (500 mL) was added 2-chloroacetyl chloride (11.1 g, 0.1 mol) drop wise at 0 C. The mixture was stirred at room temperature for 2 hrs. Then the mixture was quenched with water. The organic phase was washed with saturated brine, dried with anhydrous Na2SO4, filtered and concentrated in vacuo to give the product title compound (6.30 g) as a light yellow oil. 1H NMR (400 MHz, DMSO-d6) d 6.37 (b, 1H), 4.14-4.02 (m, 1H), 1.20 (d, J = 6.8 Hz, 6H).
299 mg	With triethylamine; In dichloromethane; at 0 - 25℃; for 2h;Inert atmosphere;	To a solution of isopropylamine (200 mg) and dry Et3N (821 mg) in 6.8 mL of dry DCM were added 2-chloroacetyl chloride (458 mg) dropwise at 0 C. After stirring 15 min at this temperature, the mixture was additionally stirred for 2 h at RT. After completion of the reaction as monitored by LCMS water was added and the organic phase was separated. The water phase was extracted two times with DCM and the combined organic layers were dried with MgS04, the solvents were removed under reduced pressure and the crude product was purified by silica gel (0887) chromatography using a gradient of ethyl acetate/cyclohexane as eluent. (0888) Yield: 299 mg MS (ES+) [M+H]+: m/e = 136.0, RT: 0.428 min
	With triethylamine; In dichloromethane; at 20℃;	General procedure: Dissolve different amine compounds in dichloromethane, add triethylamine (2.0 eq.), dropwise add chloroacetyl chloride (1.1 eq.) under an ice bath, and then continue stirring at room temperature for 2-6 h. After completed of the reaction, the mixture was extracted, and recrystallized to obtain intermediates A.

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[7]ChemMedChem,2018,vol. 13,p. 2455 - 2463.
[8]Journal of the American Chemical Society,1956,vol. 78,p. 2556,2557.
[9]Journal of the American Chemical Society,1953,vol. 75,p. 918.
[10]Tetrahedron Letters,2009,vol. 50,p. 5123 - 5125.
[11]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 6310 - 6312.
[12]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 1479 - 1483.
[13]RSC Advances,2015,vol. 5,p. 48368 - 48381.
[14]Patent: WO2016/210331,2016,A1 .Location in patent: Paragraph 0089; 0090.
[15]Patent: WO2016/210330,2016,A1 .Location in patent: Paragraph 0093-0094.
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[18]Molecules,2018,vol. 23.
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4
[ 71985-56-3 ]
[ 2895-21-8 ]

References: [1]Canadian Journal of Chemistry,1979,vol. 57,p. 1958 - 1966.

5
[ 71985-57-4 ]
[ 2895-21-8 ]

References: [1]Canadian Journal of Chemistry,1979,vol. 57,p. 1958 - 1966.

6
[ 2895-21-8 ]
[ 873-55-2 ]
[ 71985-71-2 ]

References: [1]Canadian Journal of Chemistry,1979,vol. 57,p. 1958 - 1966.

7
[ 2895-21-8 ]
[ 3454-66-8 ]
[ 2275-18-5 ]

References: [1]Journal of Organic Chemistry,1961,vol. 26,p. 2281 - 2288.

8
[ 2895-21-8 ]
[ 75-64-9 ]
[ 38630-95-4 ]

References: [1]Journal of Organic Chemistry,1973,vol. 38,p. 1645 - 1647.

9
[ 2895-21-8 ]
[ 756-80-9 ]
[ 3928-03-8 ]

References: [1]Journal of Organic Chemistry,1961,vol. 26,p. 2281 - 2288.

10
[ 2895-21-8 ]
[ 122-52-1 ]
[ 3699-79-4 ]

Yield	Reaction Conditions	Operation in experiment
34%	at 140℃; for 8h;	6.1 Synthesis of Intermediate 15A mixture of N,-isopropylchloroacetamide (1 g, 7.41 mmol) and triethyl phosphite1.6 mL, 9.09 mmol) was stirred at 140 C. for 8 h. The reaction mixture was cooled to room temperature and 200 mg sample was use to be purified by Prep HPLC to give intermediate 15 (60 mg, 34%) as a colorless oil.

References: [1]Patent: US9119853,2015,B2 .Location in patent: Page/Page column 62; 63.
[2]Journal of general chemistry of the USSR,1966,vol. 36,p. 465 - 467.
Zhurnal Obshchei Khimii,1966,vol. 36,p. 447 - 449.

11
[ 38788-38-4 ]
[ 2895-21-8 ]
[ 132638-34-7 ]

References: [1]Synthetic Communications,1990,vol. 20,p. 2579 - 2584.

12
[ 2895-21-8 ]
[ 622-32-2 ]
[ 76810-31-6 ]

References: [1]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 2720 - 2733.

13
[ 2895-21-8 ]
[ 140-89-6 ]
[ 137303-05-0 ]

References: [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,1991,vol. 46,p. 1251 - 1257.

14
[ 2895-21-8 ]
[ 1074-82-4 ]
[ 99275-58-8 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 577 - 581.

15
[ 2895-21-8 ]
[ 128-44-9 ]
[ 77696-96-9 ]

References: [1]Journal of Heterocyclic Chemistry,1983,vol. 20,p. 155 - 160.

16
[ 2895-21-8 ]
[ 74-88-4 ]
[ 125983-10-0 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1989,vol. 331,p. 243 - 262.

17
[ 2895-21-8 ]
4,9-dimethyl-6-hydroxy-2H-furo-<2,3-h>-<1>-benzopyran-2-one [ No CAS ]
N-isopropyl-<4,9-dimethy-2H-furo-<2,3-h>-<1>-benzopyran-6-yl>acetamide [ No CAS ]

References: [1]Acta poloniae pharmaceutica,1994,vol. 51,p. 475 - 477.

18
[ 7572-29-4 ]
[ 75-31-0 ]
[ 2895-21-8 ]
α-chloro-N,N'-di(iso-propyl)ethylimine [ No CAS ]
N,N'-Diisopropyl-2-isopropylamino-acetamidine [ No CAS ]
N-Isopropyl-2-isopropylamino-N-(isopropylcarbamoyl-methyl)-acetamide [ No CAS ]

References: [1]Bulletin des Societes Chimiques Belges,1995,vol. 104,p. 407 - 410.

19
[ 7572-29-4 ]
[ 75-31-0 ]
[ 2895-21-8 ]
N,N'-Diisopropyl-2-isopropylamino-acetamidine [ No CAS ]
N-Isopropyl-2-[isopropyl-(isopropylcarbamoyl-methyl)-amino]-acetamide [ No CAS ]
N-Isopropyl-2-isopropylamino-N-(isopropylcarbamoyl-methyl)-acetamide [ No CAS ]

References: [1]Bulletin des Societes Chimiques Belges,1995,vol. 104,p. 407 - 410.

20
[ 2895-21-8 ]
[ 243-59-4 ]
2-Indolo[2,3-b]quinoxalin-6-yl-N-isopropyl-acetamide [ No CAS ]

References: [1]Acta Poloniae Pharmaceutica,1995,vol. 52,p. 249 - 252.

21
[ 2895-21-8 ]
[ 23981-47-7 ]
N-isopropylcarbamoylmethyl 6-methoxy-2-naphthylacetate [ No CAS ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1995,vol. 34,p. 408 - 415.

22
[ 100-02-7 ]
[ 2895-21-8 ]
[ 98379-84-1 ]