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Cas Database

1013937-63-7

1013937-63-7

Identification

  • Product Name:VTP-27999

  • CAS Number: 1013937-63-7

  • EINECS:

  • Molecular Weight:639.10

  • Molecular Formula: C26H41ClN4O5.C2HF3O2

  • HS Code:

  • Mol File:1013937-63-7.mol

Synonyms:Carbamic acid, N-[2-[(R)-(3-chlorophenyl)[(3R)-1-[[[(2S)-2-(methylamino)-3-[(3R)-tetrahydro-2H-pyran-3-yl]propyl]amino]carbonyl]-3-piperidinyl]methoxy]ethyl]-, methyl ester, 2,2,2-trifluoroacetate (1:1);

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

  • Manufacture/Brand
  • Product Description
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  • Price
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  • Manufacture/Brand:Usbiological
  • Product Description:VTP 27999 Trifluoroacetate
  • Packaging:1mg
  • Price:$ 425
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:VTP27999Trifluoroacetate
  • Packaging:5mg
  • Price:$ 590
  • Delivery:In stock
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  • Manufacture/Brand:Tocris
  • Product Description:VTP27999trifluoroacetate ≥97%(HPLC)
  • Packaging:10
  • Price:$ 172
  • Delivery:In stock
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  • Manufacture/Brand:DC Chemicals
  • Product Description:VTP-279992,2,2-trifluoroacetate >98%
  • Packaging:250 mg
  • Price:$ 1700
  • Delivery:In stock
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  • Manufacture/Brand:DC Chemicals
  • Product Description:VTP-279992,2,2-trifluoroacetate >98%
  • Packaging:1 g
  • Price:$ 3400
  • Delivery:In stock
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  • Manufacture/Brand:DC Chemicals
  • Product Description:VTP-279992,2,2-trifluoroacetate >98%
  • Packaging:100 mg
  • Price:$ 950
  • Delivery:In stock
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  • Manufacture/Brand:ChemScene
  • Product Description:VTP-27999TFA 97.30%
  • Packaging:10mg
  • Price:$ 894
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  • Manufacture/Brand:ChemScene
  • Product Description:VTP-27999TFA 97.30%
  • Packaging:100mg
  • Price:$ 2160
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  • Manufacture/Brand:ChemScene
  • Product Description:VTP-27999TFA 97.30%
  • Packaging:50mg
  • Price:$ 1500
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  • Manufacture/Brand:Chemenu
  • Product Description:methyl(2-((R)-(3-chlorophenyl)((R)-1-(((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propyl)carbamoyl)piperidin-3-yl)methoxy)ethyl)carbamate2,2,2-trifluoroacetate 98%
  • Packaging:100mg
  • Price:$ 1252
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Relevant articles and documentsAll total 1 Articles be found

Discovery of VTP-27999, an alkyl amine renin inhibitor with potential for clinical utility

Jia, Lanqi,Simpson, Robert D.,Yuan, Jing,Xu, Zhenrong,Zhao, Wei,Cacatian, Salvacion,Tice, Colin M.,Guo, Joan,Ishchenko, Alexey,Singh, Suresh B.,Wu, Zhongren,McKeever, Brian M.,Bukhtiyarov, Yuri,Johnson, Judith A.,Doe, Christopher P.,Harrison, Richard K.,McGeehan, Gerard M.,Dillard, Lawrence W.,Baldwin, John J.,Claremon, David A.

, p. 747 - 751 (2011/12/01)

Structure guided optimization of a series of nonpeptidic alkyl amine renin inhibitors allowed the rational incorporation of additional polar functionality. Replacement of the cyclohexylmethyl group occupying the S1 pocket with a (R)-(tetrahydropyran-3-yl)

Process route upstream and downstream products

Process route

tert-butyl ((S)-1-((R)-3-((R)-(3-chlorophenyl)(2-((methoxycarbonyl)amino)ethoxy)methyl)piperidine-1-carboxamido)-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl)(methyl)carbamate trifluoroacetate

tert-butyl ((S)-1-((R)-3-((R)-(3-chlorophenyl)(2-((methoxycarbonyl)amino)ethoxy)methyl)piperidine-1-carboxamido)-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl)(methyl)carbamate trifluoroacetate

methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate
1013937-63-7

methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate

Conditions
Conditions Yield
With trifluoroacetic acid; In dichloromethane; for 0.5h;
54%
(R)-tert-butyl 3-((R)-(3-chlorophenyl)(hydroxy)methyl)piperidine-1-carboxylate
942142-74-7

(R)-tert-butyl 3-((R)-(3-chlorophenyl)(hydroxy)methyl)piperidine-1-carboxylate

methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate
1013937-63-7

methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate

Conditions
Conditions Yield
Multi-step reaction with 9 steps
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C
1.2: 0 - 20 °C
2.1: sodium tetrahydroborate / methanol / 20 °C
3.1: triethylamine / dichloromethane / 3 h / -5 - 20 °C
4.1: sodium azide / N,N-dimethyl-formamide / 16 h / 80 °C
5.1: water; triphenylphosphine / tetrahydrofuran / 16 h / 20 °C
6.1: dmap; triethylamine / dichloromethane / 0 - 5 °C
7.1: dichloromethane / 1 h / 20 °C
8.1: triethylamine / dichloromethane
9.1: trifluoroacetic acid / dichloromethane / 0.5 h
With dmap; sodium tetrahydroborate; sodium azide; water; sodium hydride; triethylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil;
(R)-tert-butyl 3-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate
884510-86-5

(R)-tert-butyl 3-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate

methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate
1013937-63-7

methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate

Conditions
Conditions Yield
Multi-step reaction with 11 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere
1.2: -78 - 20 °C / Inert atmosphere
2.1: R-CBS-oxazaborolidine / tetrahydrofuran; toluene / -15 °C / Inert atmosphere
2.2: -15 °C / Inert atmosphere
3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C
3.2: 0 - 20 °C
4.1: sodium tetrahydroborate / methanol / 20 °C
5.1: triethylamine / dichloromethane / 3 h / -5 - 20 °C
6.1: sodium azide / N,N-dimethyl-formamide / 16 h / 80 °C
7.1: water; triphenylphosphine / tetrahydrofuran / 16 h / 20 °C
8.1: dmap; triethylamine / dichloromethane / 0 - 5 °C
9.1: dichloromethane / 1 h / 20 °C
10.1: triethylamine / dichloromethane
11.1: trifluoroacetic acid / dichloromethane / 0.5 h
With dmap; sodium tetrahydroborate; n-butyllithium; sodium azide; water; sodium hydride; triethylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil;
(R)-tert-butyl 3-(3-chlorobenzoyl)piperidine-1-carboxylate
884512-09-8,1438393-11-3

(R)-tert-butyl 3-(3-chlorobenzoyl)piperidine-1-carboxylate

methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate
1013937-63-7

methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate

Conditions
Conditions Yield
Multi-step reaction with 10 steps
1.1: R-CBS-oxazaborolidine / tetrahydrofuran; toluene / -15 °C / Inert atmosphere
1.2: -15 °C / Inert atmosphere
2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C
2.2: 0 - 20 °C
3.1: sodium tetrahydroborate / methanol / 20 °C
4.1: triethylamine / dichloromethane / 3 h / -5 - 20 °C
5.1: sodium azide / N,N-dimethyl-formamide / 16 h / 80 °C
6.1: water; triphenylphosphine / tetrahydrofuran / 16 h / 20 °C
7.1: dmap; triethylamine / dichloromethane / 0 - 5 °C
8.1: dichloromethane / 1 h / 20 °C
9.1: triethylamine / dichloromethane
10.1: trifluoroacetic acid / dichloromethane / 0.5 h
With dmap; sodium tetrahydroborate; sodium azide; water; sodium hydride; triethylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil;
(R)-tert-butyl 3-((R)-(3-chlorophenyl)(2-ethoxy-2-oxoethoxy)methyl)piperidine-1-carboxylate
942142-76-9

(R)-tert-butyl 3-((R)-(3-chlorophenyl)(2-ethoxy-2-oxoethoxy)methyl)piperidine-1-carboxylate

methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate
1013937-63-7

methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate

Conditions
Conditions Yield
Multi-step reaction with 8 steps
1: sodium tetrahydroborate / methanol / 20 °C
2: triethylamine / dichloromethane / 3 h / -5 - 20 °C
3: sodium azide / N,N-dimethyl-formamide / 16 h / 80 °C
4: water; triphenylphosphine / tetrahydrofuran / 16 h / 20 °C
5: dmap; triethylamine / dichloromethane / 0 - 5 °C
6: dichloromethane / 1 h / 20 °C
7: triethylamine / dichloromethane
8: trifluoroacetic acid / dichloromethane / 0.5 h
With dmap; sodium tetrahydroborate; sodium azide; water; triethylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
(R)-tert-butyl 3-((R)-(3-chlorophenyl)(2-hydroxyethoxy)methyl)piperidine-1-carboxylate
942145-03-1

(R)-tert-butyl 3-((R)-(3-chlorophenyl)(2-hydroxyethoxy)methyl)piperidine-1-carboxylate

methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate
1013937-63-7

methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate

Conditions
Conditions Yield
Multi-step reaction with 7 steps
1: triethylamine / dichloromethane / 3 h / -5 - 20 °C
2: sodium azide / N,N-dimethyl-formamide / 16 h / 80 °C
3: water; triphenylphosphine / tetrahydrofuran / 16 h / 20 °C
4: dmap; triethylamine / dichloromethane / 0 - 5 °C
5: dichloromethane / 1 h / 20 °C
6: triethylamine / dichloromethane
7: trifluoroacetic acid / dichloromethane / 0.5 h
With dmap; sodium azide; water; triethylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
(R)-tert-butyl 3-((R)-(2-azidoethoxy)(3-chlorophenyl)methyl)piperidine-1-carboxylate
942145-05-3

(R)-tert-butyl 3-((R)-(2-azidoethoxy)(3-chlorophenyl)methyl)piperidine-1-carboxylate

methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate
1013937-63-7

methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: water; triphenylphosphine / tetrahydrofuran / 16 h / 20 °C
2: dmap; triethylamine / dichloromethane / 0 - 5 °C
3: dichloromethane / 1 h / 20 °C
4: triethylamine / dichloromethane
5: trifluoroacetic acid / dichloromethane / 0.5 h
With dmap; water; triethylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;
(R)-tert-butyl 3-((R)-(3-chlorophenyl)(2-(methylsulfonyloxy)ethoxy)methyl)piperidine-1-carboxylate
942145-04-2

(R)-tert-butyl 3-((R)-(3-chlorophenyl)(2-(methylsulfonyloxy)ethoxy)methyl)piperidine-1-carboxylate

methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate
1013937-63-7

methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate

Conditions
Conditions Yield
Multi-step reaction with 6 steps
1: sodium azide / N,N-dimethyl-formamide / 16 h / 80 °C
2: water; triphenylphosphine / tetrahydrofuran / 16 h / 20 °C
3: dmap; triethylamine / dichloromethane / 0 - 5 °C
4: dichloromethane / 1 h / 20 °C
5: triethylamine / dichloromethane
6: trifluoroacetic acid / dichloromethane / 0.5 h
With dmap; sodium azide; water; triethylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
(R)-tert-butyl 3-((R)-(3-chlorophenyl)(2-(methoxycarbonylamino)ethoxy)methyl)piperidine-1-carboxylate
942142-79-2

(R)-tert-butyl 3-((R)-(3-chlorophenyl)(2-(methoxycarbonylamino)ethoxy)methyl)piperidine-1-carboxylate

methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate
1013937-63-7

methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: dichloromethane / 1 h / 20 °C
2: triethylamine / dichloromethane
3: trifluoroacetic acid / dichloromethane / 0.5 h
With triethylamine; trifluoroacetic acid; In dichloromethane;
(R)-tert-butyl 3-((R)-(2-aminoethoxy)(3-chlorophenyl)methyl)piperidine-1-carboxylate
942142-78-1

(R)-tert-butyl 3-((R)-(2-aminoethoxy)(3-chlorophenyl)methyl)piperidine-1-carboxylate

methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate
1013937-63-7

methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-2-(methylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate trifluoroacetate

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: dmap; triethylamine / dichloromethane / 0 - 5 °C
2: dichloromethane / 1 h / 20 °C
3: triethylamine / dichloromethane
4: trifluoroacetic acid / dichloromethane / 0.5 h
With dmap; triethylamine; trifluoroacetic acid; In dichloromethane;

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