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Structure of 138377-80-7

Chemical Structure| 138377-80-7

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Product Details of [ 138377-80-7 ]

CAS No. :138377-80-7
Formula : C5H11ClN2O
M.W : 150.61
SMILES Code : O=C1NCCCC1N.[H]Cl
MDL No. :MFCD09028970
InChI Key :NLAYLURYAOXTTE-UHFFFAOYSA-N
Pubchem ID :19795138

Safety of [ 138377-80-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 138377-80-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 0
Fraction Csp3 0.8
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 2.0
Molar Refractivity 40.62
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

55.12 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.0
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

-0.05
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

-0.36
Log Po/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.

-0.41
Log Po/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

0.13
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.14

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-0.74
Solubility 27.3 mg/ml ; 0.181 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.

-0.66
Solubility 33.2 mg/ml ; 0.22 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

-0.56
Solubility 41.3 mg/ml ; 0.274 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

No
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.

-7.25 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

0.0 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)

1.57

Application In Synthesis of [ 138377-80-7 ]

* 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 [ 138377-80-7 ]

[ 138377-80-7 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 138377-80-7 ]
  • [ 270902-67-5 ]
  • [ 889214-42-0 ]
YieldReaction ConditionsOperation in experiment
83% With sodium 2-ethylhexanoic acid; In tetrahydrofuran; at 20℃; for 96h; 24.64 mg of 4 (0.087 mmol), 41.05 mg of sodium 2-ethyl-hexanoate (0.247 mmol), 20.16 mg of 15 (which may be prepared according to the procedures described in WO 2002/081480, and the content of which is incorporated herein by reference) (0.134 mmol) and 2 ml of THF are successively introduced into a 20 ml round-bottomed flask with stirring and under an argon atmosphere. Stirring is continued for 4 days at r.t. 20 ml of EtOAc are added to the reaction medium, which is then washed successively with 20 ml of NaOH solution (0.1 N), 20 ml of water and 20 ml of saturated NaCl solution. As product has visibly dissolved in the aqueous phase, this aqueous phase is extracted twice with a mixture of 50 ml of CH2Cl2 and 5 ml of MeOH. The 3 organic phases are combined, dried, filtered and then evaporated to dryness. The crude product is purified by PCC with a 93/7 CH2Cl2/MeOH mixture. 28.49 mg of product 16 are collected (Yld=83percent). TLC (90/10 CH2Cl2/MeOH): Rf=0.28 1H NMR (400 MHz, CDCl3): delta (ppm)=7.11 (d, 1H); 5.70 (d, 1H); 5.67 (m, 1H); 5.48 (dd, 1H); 4.72 (m, 1H); 4.20 (d, 1H); 4.02 (d, 1H); 3.80 (d, 1H); 3.50 (s, 1H); 3.49 (s, 3H); 3.36 (m, 2H); 2.54 (m, 2H); 1.96 (m, 2H); 1.47 (s, 6H); 1.02 (s, 9H) LCMS (ES+, 30 V): tR=2.92 mn|m/z=797+ (2M+H+); 399+ (M+H+); 341+ (M+H+[(H3C)2CO]); 841 (2 MH+HCOOH); 443 (MH+HCOOH)
  • 3
  • [ 849410-20-4 ]
  • [ 138377-80-7 ]
  • 3-[(benzylsulfonyl)(methyl)amino]-N-((1S,2S,4R)-2-[tert-butyl(dimethyl)silyl]oxy}-1-isobutyl-4-methyl-5-oxo-5-[2-oxopiperidinyl]amino}pentyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% With N-ethyl-N,N-diisopropylamine; HATU; In DMF (N,N-dimethyl-formamide); at 0 - 20℃; for 3h; [Preparation Example 116] Preparation of 3-[(benzylsulfonyl)(methyl)amino]-N-((1S,2S,4R)-2-[tert- butyl(dimethyl)silyl]oxy}-1-isobutyl-4-methyl-5-oxo-5-[(3R or 3S)-2- OXOPIPERIDINYL] AMMO} PENTVBENZAMIDE 91 mg (0. 15 mmol) of the compound obtained in Preparation Example 58 was dissolved in 5 ml of N, N-DIMETHYLFORMAMIDE and cooled to 0°C, then 34 mg (0.225 mmol) obtained in Preparation Example 115 and 86 mg (0.225 mmol) of HATU were added thereto. 0.5 ml (excess amount) of N, N-diisopropylethylamine was then added thereto and heated to room temperature, followed by stirring for 3 hours. After removing solvent by distillation under reduced pressure, the residue was dissolved in ethyl acetate and washed with water, 0.5 N hydrochloride solution, saturated sodium bicarbonate solution and sodium chloride solution. After removing solvent by distillation under reduced pressure, the product was purified by column chromatography using a 5: 95 mixture of methanol and dichloromethane to obtain 21 mg of the title compound at 20percent yield. 1H NMR (400 MHz, CDC) ; 7.82 (1H, s), 7.59 (1H, d), 7.45-7. 33 (7H, m), 6.79 (1H, d), 6.27 (1H, d), 5.48 (1H, s), 4.50-4. 20 (4H, m), 3.80 (1H, m), 3.23 (3H, s), 3.22-3. 12 (2H, m), 2.54 (1H, m), 2.28 (1H, m), 1.97 (1H, m), 1.92-1. 48 (6H, m), 1.39 (1H, m), 1.17 (3H, d), 0.98 (3H, d), 0.97 (3H, d), 0.91 (9H, s), 0.12 (3H, s), 0.11 (3H, s)
  • 4
  • [ 138377-80-7 ]
  • [ 1892-22-4 ]
YieldReaction ConditionsOperation in experiment
Example 10 ; 3-[({4-[(3-chloro-2-fluorophenyl) amino]-7-methoxyquinazolin-6- yl} methyl) amino] piperidin-2-one; (Process (a)); 4- [ (3-Chloro-2-fluorophenyl) amino]-7-methoxyquinazoline-6-carbaldehyde was coupled with 3-amino-piperidin-2-one (prepared by converting <strong>[138377-80-7]3-amino-piperidin-2-one hydrochloride</strong> to the free-base form) using an analogous method to that described for the equivalent step in Example 1 to give the title compound ; 1H NMR spectrum : (DMSO d6) 1. 5= (m, 1H), 1.68 (m, 1H), 1.84 (m, 1H), 2.16 (m, 1H), 2.73 (brs, 1H), 3.05 (dd, 1H), 3.13 (m, 2H), 3.84 (d, 1H), 3.93 (d, 1H), 3.98 (s, 3H), 7.21 (s, 1H), 7.28 (t, 1H), 7.48 (t, 1H), 7.53 (m, 2H), 8.35 (s, 1H), 8.44 (s, 1H), 9.80 (s, 1H); Mass Spectrum : (M+H) +430.
With AMBERLYST A21; In methanol; at 20℃; To a solution of <strong>[138377-80-7]3-aminopiperidin-2-one hydrochloride</strong> (1.50 g) in methanol (10 mL) was added AMBERLYST (registered trademark) A21 (750 mg) at room temperature. The reaction mixture was stirred at room temperature overnight, theinsoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. To a solution of the residue in ethanol (20 mL) was added 4-thioxothiazolidin-2-one (1.330 g) at room temperature. The reaction mixture wasstirred at room temperature overnight, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate) . To a solution of the residue and l-[2,4- bis (trifluoromethyl) benzyl] piperidine-4-carbaldehyde (1018 mg) in 2-propanol (10 mL) was added piperidinium acetate (436 mg) at room temperature. The reaction mixture was stirred at 60°C overnight, and the solvent was evaporated under reducedpressure. The residue was purified by silica gel columnchromatography (NH, methanol/ethyl acetate) and recrystallized from ethyl acetate/diisopropyl ether to give the titlecompound (530 mg) .¾ NMR (300 MHz, DMSO-d6) delta 1.38-1.59 (2H, m) , 1.68-1.91 (5H, m) , 2.01-2.27 (4H, m) , 2.69-2.84 (2H, m) , 3.17 (2H, brs) , 3.71 (2H, s), 4.43-4.55 (1H, m) , 6.89 (1H, d, J = 8.8 Hz), 7.83 (1H, brs), 7.98 (1H, s) , 8.02-8.12 (2H, m) , 9.34 (1H, brs).MS (ESI+) : [M+H]+ 535.1.
  • 5
  • [ 857265-17-9 ]
  • [ 138377-80-7 ]
  • N-{3-[(2-aminopyrimidin-5-yl)ethynyl]phenyl}-N'-(2-oxopiperidin-3-yl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With triethylamine; In tetrahydrofuran; at 80℃; for 24h; Phenyl {3-[(2-aminopyrimidin-5-yl) ethynyl] phenyl} carbamate (Example 23) (50 mg), 3- amino-piperidin-2-one hydrochloride (46 mg) and triethylamine (0.06 mL) in THF (2 mL) were heated at 80°C for 24 hours. The reaction mixture was concentrated in vacuo and the solid triturated with water then diethyl ether, dried under vacuum at 60°C to give the title compound as a beige solid (41 mg, 77percent) ; 'H NMR (DMSO-d6) 1.49-1. 62 (m, 1H), 1.71-1. 82 (m, 2H), 2.16-2. 28 (m, 1H), 3.10-3. 18 (m, 2H), 3.95-4. 04 (m, 1H), 6.42-6. 48 (d, 2H), 6.98-7. 04 (m, 1H), 7.09 (s, 2H), 7.20-7. 31 (m, 2H), 7.65 (s, 2H), 8.41 (s, 2H), 8.85 (s, 1H) ; MS m/e MH 351.
  • 6
  • [ 138377-80-7 ]
  • [ 98-59-9 ]
  • [ 91558-30-4 ]
YieldReaction ConditionsOperation in experiment
69% With potassium carbonate; Reference Example 1 : 3-(4,-MethylbenzenesuIfonylamino)tetrahydropyridin-2- one:; <strong>[138377-80-7]3-aminotetrahydropyridin-2-one hydrochloride</strong> (10 mmol), K2C03 (30 mmol) and 4- methylbenzenesulfonyl chloride (10 mmol) were reacted according to the above procedure to give the product (1.64 g, 69percent):Vmax/cm"1 3224, 1658 (secondary CONH, lactam), 1598, 1494 (aromatic ring), 1324, 1161 (S02-N), 814, 802 (pam-disubstituted benzene). NMR: deltaEta (400MHz, CDC13) 7.77 (2H, d, J 8.5, ortho-U), 7.29 (2H, d, J 8.0, meta- H), 5.79 (1H, br d, J 1.0, C7H7-S02NH), 5.56 (1Eta, br s, CONH-CH2), 3.49-3.42 (1H, m, CH-CO), 3.31-3.24 (2H, m, CH2NH), 2.53-2.45 (1H, m, lactam CH2), 2.40 (3H, s, CH3), 1.97-1.88 (1H, m, lactam CH2), 1.88-1.68 (2H, m, lactam CH2). 13C NMR: 6C (100MHz, CDC13) 172.2 (lactam C=0), 142.2 (ipso-C), 136.2 (para-C), 129.7 (aromatic CH), 127.3 (aromatic CH), 53.3 (CH-CO), 42.0 (C3/4-NH), 29.6 (lactam CH2), 28.6 (lactam CH2), 27.9 (lactam CH2), 21.5 (CH3).HRMS (+ESI) C,2H16N203S + Na+: calcd 291.0774; found 291.0777.
  • 7
  • [ 10400-19-8 ]
  • [ 138377-80-7 ]
  • [ 1352127-79-7 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In dichloromethane; water; Reference Example 11 : 3-(Pyridin-3'-carbonylamino)tetrahydropyridin-2- one:; Oxalyl chloride (20 mmol) was added to a solution of nicotinic acid (10 mmol) in DCM (40 mL), along with one drop of catalytic DMF. The reaction mixture was stirred for 16 h and then the solvent was removed under high vacuum. The resulting crystals were dissolved in DCM (10 mL). In a separate flask, 3- aminotetrahydropyridin-2-one hydrochloride (10 mmol) and 2C03 (30 mmol) were added to water (30 mL) and stirred, giving a solution to which the acid chloride solution was added. The reaction was worked-up as above to give the product (0.10 g, 5percent):Vmax cm"' 3257 (N-H, amide), 1642, 1541 (secondary CONH, lactam, NH), 1591 , 1479 (aromatic pyridine ring). NMR: deltaEta (400MHz, CDC13) 9.03 (I H, d, J 2.0, 2'-aryl CH), 8.71 (I H, dd, J 5.0, 1.5, 6'-aryl CH), 8.12 (I H, dt, J 8.0, 2.0, 4'-aryl CH), 7.36 (IH, dd, J 8.0, 5.0, 5'-aryl CH), 7.27 (I H, br d, J2.0, C5H4N-CONH), 5.91 (IH, br s, CONH-CH2), 4.45 (IH, dt, J 1 1.0, 5.5, CH-CO), 3.44-3.32 (2H, m, CH2NH), 2.72 (IH, dt, J 14.5, 4.5, NHCH- C 2), 2.06-1.93 (2H, m, lactam CH2), 1.70-1.54 (I H, m, lactam CH2).13C NMR: 6c (100MHz, CDC13) 171.8 (lactam C=0), 166.0 (aryl C=0), 152.5 (aryl N- CH), 148.6 (aryl N-CH), 135.3 (ortho-C(-C )), 133.4 (ipso-C), 123.6 (meta-C), 51.2 (CH-CO), 42.0 (CH2-NH), 27.3 (lactam CH2), 21.3 (lactam CH2). HRMS (+ESI) C, ,H 13N302 + H+: calcd 220.1081 ; found 220.1085.
  • 8
  • [ 138377-80-7 ]
  • [ 98-88-4 ]
  • [ 3328-28-7 ]
YieldReaction ConditionsOperation in experiment
74% Reference Example 1: 3-(Benzoylamino)tetrahydropyridin-2-one:; <strong>[138377-80-7]3-aminotetrahydropyridin-2-one hydrochloride</strong> (10 mmol) and K2C03 (30 mmol) were added to water (20 mL) and stirred. A solution of benzoyl chloride (10 mmol) in CH2C12 (10 mL) was added and the reaction was stirred overnight at room temperature in an inert atmosphere (using dinitrogen). The reaction was extracted with CH2C12 (3 chi 50 mL), and the combined organic layers where then dried (Na2S04) and reduced in vacuo to give a crude product which was recrystallised from CH2C12 / petroleum ether (bp 40-60 °C) to give the product (1.62 g, 74percent): Vmax/cm"1 3250 (N-H, amide), 1664, 1633, 1538 (secondary CONH, lactam), 1605, 1578, 1486 (aromatic ring), 766, 715, 704, 690 (monosubstituted benzene ring). NMR: deltaEta (400MHz, CDC13) 7.80 (2H, br d, J 7.0, ortho-H), 7.47-7.40 (1 H, m, para-U), 7.42-7.39 (1 H, m, C6H5-CONH), 7.40-7.31 (2H, m, meta-W), 6.78 (1 H, br s, CONH-CH2), 4.41 (1 H, dt, J 1 1.5, 5.5, CH-CO), 3.36-3.23 (2H, m, CH2NH), 2.59 (1 H,22P66854. WOO L Spec as Hied 8.06.1 1 dq, J 13.0, 4.5, NHCH-CH;), 1.94-1.81 (2H, m, lactam CH2), 1.64 (IH, tt, J 12.5, 8.0, NHCH-CH^).13C NMR: 5C (100MHz, CDC13) 171.9 (lactam C=0), 167.4 (aryl C=0), 134.0 (ipso- C), 131.4 (ortho-C), 128.3 (meta-C), 127.0 (para-C), 50.8 ( H-CO), 41.5 (CH2NH), 27.0 (lactam CH2), 20.9 (lactam CH2).HRMS (+ESI) Ci2H,4N202 + Na+: calcd 241.0947; found 241.0950.
  • 9
  • [ 24424-99-5 ]
  • [ 138377-80-7 ]
  • [ 99780-98-0 ]
YieldReaction ConditionsOperation in experiment
3.41 g With triethylamine; In tetrahydrofuran; at 20℃; To a solution of <strong>[138377-80-7]3-aminopiperidin-2-one hydrochloride</strong> (3.49 g) and triethylamine (6.20 mL) in THF (50 mL) was added di-tert-butyl bicarbonate (6.07 g) at room temperature. The reaction mixture was stirred at room temperature overnight, water was added, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (3.41 g) .XH NMR (300 MHz, DMSO-d6) delta 1.38 (9H, s) , 1.53-2.03 (4H, m) , 3.09 (2H, brs), 3.68-3.91 (1H, m) , 6.83 (1H, d, J = 8.1 Hz), 7.48 (1H, brs) .
  • 10
  • [ 138377-80-7 ]
  • [ 13292-22-3 ]
  • C43H57N3O13 [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% General procedure: 3-Formyl-rifamycin SV (RAL)was purchased from LKT Laboratories Inc. (>98%). RAL (250.0mg, 0.34 mmol) was dissolved in 50 ml CH2Cl2 and afterthe addition of catalyst (0.025 mmol HCl/EtOH) respective mixtures wereprepared with each of the following compounds taken separately: 1-adamantylamine,1-methylpiperazine,1-(2-pyridyl)piperazine,1-(4-fluorobenzyl)piperazine,1-(2,4,6-trimethylbenzyl)piperazine, 1-bis(4-fluorophenyl)methylpiperazine, 1-(ethanesulfonyl)piperazine, 1-(methylsulfonyl)piperidin-4-amine, 4-(dimethylamino)-piperidine,1-(4-pyridyl)piperazine, 1-(2-pyrimidyl)piperazinedihydrochloride, 1,9-dimethyl-1,4,9-triazaspiro[5.5]undecanetrihydrochloride, 3,4-dihydro-2H-spiro[isoquinoline-1,4?-piperidine],n-piperidin-4-yl-methanesulfonamide,1-[3-(trifluoromethyl)pyrid-2-yl]piperazine,1-(cyclohexylmethyl)-4-piperidinamine,1,4?-bipiperidine-4-carboxylic acid dihydrochloride, (4-amino-1-piperidinyl)acetic acid dihydrochloride, 2-oxo-2-(1-piperidinyl)ethanamine,1-(2-amino-ethyl)-pyrrolidin-2-one,4-amino-1-Boc-piperidine, 3-amino-2-piperidinonehydrochloride, 1-acetyl-4-aminopiperidine hydrochloride in1 ml of CH3OH. Amines containinghydrochloride were neutralized with an equivalent amount of KOH/EtOH (0.06 mmolor 0.12 mmol or 0.18 mmol) solution. The mixtures were stirred at 40C for halfan hour and after that 3/4 of the solvent volume was distilled off. To thecooled reaction mixture (room temperature) the reductant NaBH3CN (13mg, 0.15 mmol) was added portionwise over 1 min. The reaction mixture wasstirred for one hour. Next the reaction mixture was evaporated to dryness,dissolved in 50 ml of CH2Cl2 and extracted twice with 50ml of water and brine (theses stages were omitted for reactions with1,4?-bipiperidine-4-carboxylic acid dihydrochloride,(4-amino-1-piperidinyl)acetic acid dihydrochloride). The separated organiclayer was evaporated and the synthesized derivatives of 3-formylrifamycin SV(compounds 1-23) were next purified by column chromatography with silicagel (25 cm × 1 cm, silica gel 60, 0.040-0.063 mm/230-400 mesh ASTM, Fluka) withdichloromethane/methanol (from 200:1 to 3:1) as an eluent.
 

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Technical Information

Categories

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[ 138377-80-7 ]

Amides

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A476158 [24666-56-6]

3-Aminopiperidine-2,6-dione hydrochloride

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(R)-3-Aminoazepan-2-one hydrochloride

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