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[ CAS No. 186550-13-0 ] {[proInfo.proName]}

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Chemical Structure| 186550-13-0
Chemical Structure| 186550-13-0
Structure of 186550-13-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 186550-13-0 ]

CAS No. :186550-13-0 MDL No. :MFCD01861220
Formula : C9H18N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :CMIBWIAICVBURI-UHFFFAOYSA-N
M.W : 186.25 Pubchem ID :2756370
Synonyms :

Calculated chemistry of [ 186550-13-0 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.89
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 54.49
TPSA : 55.56 Ų

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) : -7.17 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.32
Log Po/w (XLOGP3) : 0.37
Log Po/w (WLOGP) : 0.57
Log Po/w (MLOGP) : 0.56
Log Po/w (SILICOS-IT) : 0.04
Consensus Log Po/w : 0.77

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.03
Solubility : 17.4 mg/ml ; 0.0934 mol/l
Class : Very soluble
Log S (Ali) : -1.1
Solubility : 14.7 mg/ml ; 0.0791 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.64
Solubility : 43.0 mg/ml ; 0.231 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.6

Safety of [ 186550-13-0 ]

Signal Word:Danger Class:8,6.1
Precautionary Statements:P210-P264-P270-P273-P280-P301+P310+P330-P305+P351+P338+P310-P370+P378-P403+P235-P405-P501 UN#:2922
Hazard Statements:H227-H301-H318-H401 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 186550-13-0 ]

* 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 [ 186550-13-0 ]
  • Downstream synthetic route of [ 186550-13-0 ]

[ 186550-13-0 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 186550-13-0 ]
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  • [ 147081-49-0 ]
Reference: [1] Advanced Synthesis and Catalysis, 2008, vol. 350, # 6, p. 807 - 812
  • 2
  • [ 862906-31-8 ]
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YieldReaction ConditionsOperation in experiment
82% With hydrogen In methanol for 16 h; Step (ii): Preparation of compound of formula (49)To a stirred solution of compound of formula (48) ( 1.1 5 grams, 4.16 mmol) in methanol ( 16.6 mL) was added 10 percent Pd/C (345 mg). Hydrogen pressure was applied through a double- layered balloon and the reaction was stirred for 16 hours. The reaction was filtered through a small pad of celite and the filtrate was removed under reduced pressure. The crude product was purified by silica gel flash column chromatography to obtain compound of formula (49) (640 mg). Yield: 82 percent.-NMR (CDCI3): δ 3.65-3.45 (m, 3H), 3.45-3.33 (m, 1H), 3.20-3.0 (m, 1H), 2.12-2.02 (m, 1H), 1.80-1.65 (m, 1 H), 1.46 (s, 9H).Mass (m/z): 187 [M+LT|.
Reference: [1] Patent: WO2005/77924, 2005, A1, . Location in patent: Page/Page column 76
[2] Patent: WO2011/30349, 2011, A1, . Location in patent: Page/Page column 36-37
  • 3
  • [ 113451-52-8 ]
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YieldReaction ConditionsOperation in experiment
73% With hydrogen In methanol for 3 h; Triethylamine (0.75 mL, 5.34 mmol) and methanesulfonyl chloride (0.31 mL, 4.00 mmol) were added to a solution of tert-butyl 3-hydroxypyrrolidine-1-carboxylate (500 mg, 2.67 mmol) in tetrahydrofuran (20 mL) at 0°C and stirred at the same temperature for 1.5 hours. Water and ethyl acetate were added to the reaction mixture, followed by extraction with ethyl acetate, and the extract solution was dried over anhydrous magnesium sulfate. The concentration residue was dissolved in N-methylpyrrolidinone (20 mL), followed by adding thereto sodium azide (520.8 mg, 8.01 mmol) at 0°C, and the resulting mixture was stirred with heating at 80°C for 3 hours. After the reaction mixture was cooled to 0°C, water and diethyl ether were added thereto, followed by two runs of extraction with diethyl ether, and the extract solution was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain an azide. To a solution of this azide in methanol (50 mL) was added palladium-carbon (250 mg) under a nitrogen atmosphere, and the resulting mixture was stirred for 3 hours under a hydrogen atmosphere. The reaction mixture was filtered by the use of Celite and the filtrate was distilled under reduced pressure to remove the solvent. The residue was purified by a silica gel chromatography to obtain tert-butyl 3-aminopyrrolidine-1-carboxylate (365.6 mg, 73percent).
Reference: [1] Patent: EP1500643, 2005, A1, . Location in patent: Page 67
  • 4
  • [ 325775-36-8 ]
  • [ 186550-13-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 1, p. 94 - 104
[2] Patent: US2003/229226, 2003, A1, . Location in patent: Page 16-17
  • 5
  • [ 24424-99-5 ]
  • [ 79286-79-6 ]
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YieldReaction ConditionsOperation in experiment
98% at 20℃; for 1 h; The starting materials were prepared as follows : 3RS-AMINO-PYRROLIDINE-1-CARBOXYLIC ACID TEFF-BUTYL ESTER To a solution of 3-aminopyrrolidine (0. 86 g, 10 MMOL) in CHCI3 (50 mi) at 0 C was added dropwise a solution of di-t-butyl dicarbonate ((BOC) 2O ; 2. 06 g, 10 MMOL) in CHCI3 (50 ML). The mixture stirred at room temperature for 1 hour, and then washed with brine, dried over K2CO3, filtered, and concentrated to give 1. 8 g of yellow oil in 98percent yield, which was used without further purification. 'H NMR : 8 3. 60-3. 28 (m, 4H), 3. 02 (m, 1 H), 2. 04 (m, 1 H), 1. 64 (m, 1 H), 1. 45 (s, 9H), 1. 45-1. 20 (m, 2H)
Reference: [1] Patent: WO2004/74283, 2004, A1, . Location in patent: Page 38
[2] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 3, p. 1237 - 1240
  • 6
  • [ 6627-89-0 ]
  • [ 79286-79-6 ]
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YieldReaction ConditionsOperation in experiment
98% for 24 h; Intermediate 138; 1 ,1 -dimethylethyl 3-amino-1 -pyrrolidinecarboxylate; 3-pyrrolidinamine (500 mg, 5.80 mmol), Tert-butyl phenyl carbonate (1.24 g, 6.38 mmol) was dissolved in DMF (5 ml) and stirred for 24 hours. Water and HCI 1 N was added until pH=3. The mixture was washed with dichloromethane (2 times). NaOH 1 N was added to the aqueous phase until pH=1 1-12 and was extracted with dichloromethane (4 times). The <n="94"/>organic phase was dried over Na2SC>4, filtered and evaporated to give the title compound as light orange liquid (1.063 g, 98percent). LC/MS : m/z 187 (M+23)+, Rt: 1.54 min.
Reference: [1] Patent: WO2009/47240, 2009, A1, . Location in patent: Page/Page column 92-93
  • 7
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Reference: [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 1, p. 94 - 104
  • 8
  • [ 122684-33-7 ]
  • [ 186550-13-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 1, p. 94 - 104
  • 9
  • [ 24424-99-5 ]
  • [ 186550-13-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 15, p. 5241 - 5251
  • 10
  • [ 101385-93-7 ]
  • [ 186550-13-0 ]
Reference: [1] Patent: WO2011/30349, 2011, A1,
  • 11
  • [ 24424-99-5 ]
  • [ 186550-13-0 ]
Reference: [1] Patent: EP1500643, 2005, A1,
  • 12
  • [ 83220-73-9 ]
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Reference: [1] Patent: EP1500643, 2005, A1,
  • 13
  • [ 141699-57-2 ]
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Reference: [1] Patent: EP1500643, 2005, A1,
  • 14
  • [ 186550-13-0 ]
  • [ 101385-93-7 ]
  • [ 147081-49-0 ]
Reference: [1] Advanced Synthesis and Catalysis, 2008, vol. 350, # 6, p. 807 - 812
  • 15
  • [ 186550-13-0 ]
  • [ 454712-26-6 ]
Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 17, p. 3189 - 3202
[2] Patent: CN108727343, 2018, A,
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