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[ CAS No. 60421-23-0 ] {[proInfo.proName]}

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Chemical Structure| 60421-23-0
Chemical Structure| 60421-23-0
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Product Details of [ 60421-23-0 ]

CAS No. :60421-23-0 MDL No. :MFCD03840364
Formula : C7H14ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :OPUJUITUYWGUEP-UHFFFAOYSA-N
M.W : 179.64 Pubchem ID :11513856
Synonyms :

Calculated chemistry of [ 60421-23-0 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.86
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 44.64
TPSA : 52.32 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.64 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.07
Log Po/w (WLOGP) : 1.23
Log Po/w (MLOGP) : 0.69
Log Po/w (SILICOS-IT) : 0.77
Consensus Log Po/w : 0.75

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.5
Solubility : 5.73 mg/ml ; 0.0319 mol/l
Class : Very soluble
Log S (Ali) : -1.76
Solubility : 3.12 mg/ml ; 0.0174 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.95
Solubility : 20.2 mg/ml ; 0.112 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.51

Safety of [ 60421-23-0 ]

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 [ 60421-23-0 ]

* 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 [ 60421-23-0 ]
  • Downstream synthetic route of [ 60421-23-0 ]

[ 60421-23-0 ] Synthesis Path-Upstream   1~9

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Reference: [1] ACS Combinatorial Science, 2018, vol. 20, # 1, p. 35 - 43
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YieldReaction ConditionsOperation in experiment
100% With thionyl chloride In methanol at -15 - 20℃; To a suspension of 1-aminocyclopentanecarboxylic acid, (675 g, 5.23 mol, 1.0 equiv.) in MeOH (6.5 L) held at -15° C. with an ice/MeOH bath was added SOCl2 (687 mL, 9.4 mol, 1.8 equiv.), dropwise at such a rate that the reaction temp. did not exceed 7° C. After the addition was complete, cooling was removed, the reaction was allowed to stir at room temp. overnight, then was concentrated under reduced pressure. The residue was treated with CH2Cl2 (1 L) and concentrated under reduced pressure to afford methyl 1-aminocyclopentanecarboxylate HCl salt as a white solid (938 g, 100percent): 1H NMR (CD3OD) d 1.87-1.94 (m, 8H), 3.83 (s, 3H); NMR (DMSO-d6) δ1.67-1.71 (m, 2H), 1.83-1.98 (m, 4H), 2.06-2.14 (m, 2H), 3.73 (s, 3H), 8.81 (br s 3). This material was used in the next step without further purification
98% at 20℃; for 3 h; Cooling with ice 1-aminocyclopentanecarboxylic acid (3.5 g, 26.9 mmol) and methanol (100 ml) were charged. An ice bath was set and thionyl chloride (3.9 ml, 53.9 mmol) was slowly added thereto. Then, the ice bath was removed, and the mixture was stirred at room temperature for 3 hours. The resultant product was vacuum-distilled to remove a solvent, and dried in a 60 oven so as to obtain methyl-1-aminocyclopentanecarboxylate hydrochloride (4.74 g, 26.4 mmol, 98 percent).[823] 1H NMR (400 MHz, DMSO-d6) δ 8.76 (br, 3H), 3.75 (s, 3H), 2.12 (m, 2H), 1.88 (m, 4H), 1.72 (m, 2H).
98% at 20℃; for 3 h; Inert atmosphere Preparation Example 1
Synthesis of N-4-(1-(3-chloro-2-methylphenylsulfonamido)cyclopentanecarboxyamido)adamantane-1-carboxyamide (compound 167)
1-aminocyclopentanecarboxylic acid (3.5 g, 26.9 mmol) and methanol (100 ml) were charged.
An ice bath was set and thionyl chloride (3.9 ml, 53.9 mmol) was slowly added thereto.
Then, the ice bath was removed, and the mixture was stirred at room temperature for 3 hours.
The resultant product was vacuum-distilled to remove a solvent, and dried in a 60° C. oven so as to obtain methyl-1-aminocyclopentanecarboxylate hydrochloride (4.74 g, 26.4 mmol, 98percent).
1H NMR (400 MHz, DMSO-d6) δ 8.76 (br, 3H), 3.75 (s, 3H), 2.12 (m, 2H), 1.88 (m, 4H), 1.72 (m, 2H).
97% at 20℃; 1-Amino-l-cyclopentanecarboxylic acid (5.00 g, 38.8 mmol) was dissolved in methanol (100 mL) and then thionyl chloride (9.25 g, 77.7 mmol) was added dropwise with stirring. The resulting mixture was stirred overnight at room temperature and then concentrated in vacuo which left a white solid. The solid was tritruated in ethyl ether, filtered, and dried to give 6.78 g (97 percent) of methyl 1-amino- 1-cyclopentanecarboxylate hydrochloride as a white solid. 1H NMR was consistent with product. ESMS (M+1) 144.2
97% for 18 h; 1-Aminocyclopentanecarboxylic acid (1.00 g, 7.74 mmol) was added to a solution of acetyl chloride (0.60 mL, 8.44 mmol) in methanol (10 mL). The reaction mixture was allowed to stir for EPO <DP n="37"/>18 h and then concentrated under reduced pressure. This yielded 1.35 g (97percent) of the title compound. 1H NMR (400 MHz, CD3OD) δ 1.80-2.00 (m, 6H), 2.34-2.39 (m, 2H), 3.82 (s, 3H).
91% Reflux Example 2.1
1-aminocyclopentanecarboxylic acid methyl ester hydrochloride
Prepared as a white powder following the general procedure previously described using cycloleucine and methanol.
Yield: 91percent
Rf (dichloromethane/methanol 9/1): 0.5
MP: 157-159° C. IR: νCO: 1742 cm-1
NMR 1H (DMSO-d6): 1.68-1.84 (m, 6H); 2.04 (m, 2H); 3.71 (s, 3H).
Example 2General Procedure for the Preparation of Amino Acid EstersAminocarboxylic acid (1eq) was added at 0° C. to the appropriate alcohol (methanol or ethanol) and the mixture was saturated with anhydrous hydrochloric acid. Thionyl chloride was then added drop by drop. The reaction mixture was stirred at reflux for 12 hours. The reaction mixture was concentrated under reduced pressure and diethyl ether was added to the crude residue. The resulting powder was filtered and washed with diethyl ether.
89%
Stage #1: at 0℃; for 1 h;
Stage #2: for 6 - 16 h; Heating / reflux
To a stirring solution of anhydrous alcohol (10 mol eq. ) was added thionyl chloride (2 mol eq. ) at 0° C, and the resulting solution stirred for 1 hr. After warming to room temperature, the appropriate amino acid (1 mol eq) was added and the reaction heated at reflux for 6-16 hrs. Removal of solvent and recrystallisation from methanol/ether gave the amino ester hydrochloride salts.; This was synthesised according to Standard Procedure 1, using 1-AMINO-1- cyclopentanecarboxylic acid (3.876 g, 30 mmol) with thionyl chloride (4.44 mL, 45 mmol, ) and anhydrous methanol (15.5 mL). The product was isolated as a white solid (4.81 g, yield 89percent). 'H-NMR (CDC13 ; 300 MHz): 8 9.1 (3H, bs, NH3+Cl), 3.85 (3H, s, OCH3), 2.3-2. 2 (4H, m, 4H cyclopentane), 2. 15 (2H, 2H cyclopentane), 1.95 (2H, m, 2H cyclopentane). 13C-NMR (CDCl3 ; 75 MHz): 8 26.6 (2CH2 cyclopent), 38.1 (2CH2 cyclopent), 54.8 (CH30), 66.6 (cyclopentane), 174.1 (COOMe).
87% at 0℃; General procedure: Thionyl chloride (10 mL) was slowly added to a cold suspension solution of the appropriate aminoacid (50 mmol) in methanol (50 mL) at 0 °C. The reaction mixture was stirred for 8–10 h and thenconcentrated on a rotary evaporator. The white precipitate formed was washed with anhydrous etherand then dried under vacuum. All data agreed with the reported data [43,44].
77% for 1 h; Heating / reflux Example 10; Methyl 1-[(1-(2,4-dichlorophenyl)-4-methyl-5-{4[(propylsulfonyl)oxy]phenyl}-1H- pyrazol-3-yl) carbonvl1ammo} cvclopentanecarboxylate; Step A Methyl 1-aminocyclopentanecarboxylate hydrochloride; Thionyl chloride (1.5 ml) was dissolved in methanol (15 ml) and poured over 1- aminocyclopentanecarboxylic acid (100 mg, 0.774 mmol). The mixture was refluxed 1 hour. The solvent was evaporated to give the product (107 mg, 77percent). 'H NMR (399.964 MHz) 8 9.00-8. 60 (br, 3H), 3.79 (s, 3H), 2.23 (s, 4H), 2.14-2. 00 (m, 2H), 1.90-1. 76 (m, 2H).
77% for 1 h; Heating / reflux Thionyl chloride (1.5 ml) was dissolved in methanol (15 ml) and poured over 1- Q aminocyclopentanecarboxylic acid (100 mg, 0.774 mmol). The mixture was refluxed 1 hour. The solvent was evaporated to give the product (107 mg, 77percent).1H NMR (399.964 MHz) δ 9.00-8.60 (br, 3H), 3.79 (s, 3H), 2.23 (s, 4H), 2.14-2.00 (m,2H), 1.90-1.76 (m, 2H).

Reference: [1] Patent: US6353006, 2002, B1, . Location in patent: Page column 31
[2] Patent: WO2013/19091, 2013, A2, . Location in patent: Paragraph 821-823
[3] Patent: US2014/206875, 2014, A1, . Location in patent: Paragraph 0449-0451
[4] Patent: WO2003/87069, 2003, A2, . Location in patent: Page/Page column 103-104
[5] Patent: WO2006/44775, 2006, A2, . Location in patent: Page/Page column 35-36
[6] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 8, p. 1942 - 1944
[7] Patent: US2010/4159, 2010, A1, . Location in patent: Page/Page column 36
[8] Patent: WO2005/12327, 2005, A2, . Location in patent: Page/Page column 18; 20
[9] Molecules, 2013, vol. 18, # 12, p. 14747 - 14759
[10] Patent: WO2005/80343, 2005, A2, . Location in patent: Page/Page column 48
[11] Patent: WO2007/20388, 2007, A1, . Location in patent: Page/Page column 46
[12] Journal of Medicinal Chemistry, 1984, vol. 27, # 12, p. 1663 - 1668
[13] Heterocycles, 1991, vol. 32, # 10, p. 1879 - 1895
[14] J. Med. Chem., 1996, vol. 39, # 3, p. 773 - 780
[15] Journal of the American Chemical Society, 1997, vol. 119, # 49, p. 11807 - 11816
[16] Patent: US2007/265225, 2007, A1, . Location in patent: Page/Page column 49
[17] Patent: US2012/270881, 2012, A1, . Location in patent: Page/Page column 116
[18] Journal of the American Chemical Society, 2016, vol. 138, # 25, p. 7939 - 7945
[19] Patent: WO2009/120652, 2009, A2, . Location in patent: Page/Page column 71
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Reference: [1] Patent: US2004/266856, 2004, A1, . Location in patent: Page/Page column 39
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Reference: [1] Patent: US6407116, 2002, B1,
[2] Patent: US2002/82218, 2002, A1,
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Reference: [1] Patent: US3966796, 1976, A,
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Reference: [1] Patent: WO2008/4698, 2008, A2, . Location in patent: Page/Page column 82
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Reference: [1] Journal of Medicinal Chemistry, 1984, vol. 27, # 12, p. 1663 - 1668
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 13, p. 3449 - 3453
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 13, p. 3449 - 3453
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