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Cas Database

646502-53-6

646502-53-6

Identification

  • Product Name:L-Valinamide, N-[[[4-[[N-[6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-L-valyl-N 5-(aminocarbonyl)-L-ornithyl]amino]phenyl]methoxy]carbonyl]-N-methyl-L- valyl-N-[(1S,2R)-4-[(2S)-2-[(1R,2R)-3-[[(1R,2S)-2-hydroxy-1-methyl-2-p henylethyl]amino]-1-methoxy-2-methyl-3-oxopropyl]-1-pyrrolidinyl]-2-met hoxy-1-[(1S)-1-methylpropyl]-4-oxobutyl]-N-methyl-

  • CAS Number: 646502-53-6

  • EINECS:

  • Molecular Weight:1316.63

  • Molecular Formula: C68H105N11O15

  • HS Code:

  • Mol File:646502-53-6.mol

Synonyms:

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  • Manufacture/Brand:DC Chemicals
  • Product Description:VcMMAE >99%
  • Packaging:1 g
  • Price:$ 2600
  • Delivery:In stock
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  • Manufacture/Brand:DC Chemicals
  • Product Description:VcMMAE >99%
  • Packaging:250 mg
  • Price:$ 1400
  • Delivery:In stock
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  • Manufacture/Brand:Crysdot
  • Product Description:VcMMAE 98+%
  • Packaging:5mg
  • Price:$ 830
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  • Manufacture/Brand:Crysdot
  • Product Description:VcMMAE 98+%
  • Packaging:10mg
  • Price:$ 1250
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  • Manufacture/Brand:Crysdot
  • Product Description:VcMMAE 98+%
  • Packaging:50mg
  • Price:$ 3748
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  • Manufacture/Brand:ChemScene
  • Product Description:VcMMAE 99.89%
  • Packaging:1g
  • Price:$ 3950
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  • Manufacture/Brand:ChemScene
  • Product Description:VcMMAE 99.89%
  • Packaging:250mg
  • Price:$ 1580
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  • Manufacture/Brand:Chemenu
  • Product Description:[4-[[(2S)-5-(carbamoylamino)-2-[[(2S)-2-[6-(2,5-dioxopyrrol-1-yl)hexanoylamino]-3-methylbutanoyl]amino]pentanoyl]amino]phenyl]methylN-[(2S)-1-[[(2S)-1-[[(3R,4S,5S)-1-[(2S)-2-[(1R,2R)-3-[[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]amino]-1-methoxy-2-methyl-3-o 95%+
  • Packaging:1g
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  • Manufacture/Brand:BroadPharm
  • Product Description:MC-Val-Cit-PAB-MMAE 98%
  • Packaging:10 MG
  • Price:$ 410
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  • Manufacture/Brand:BroadPharm
  • Product Description:MC-Val-Cit-PAB-MMAE 98%
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Relevant articles and documentsAll total 18 Articles be found

EFFICIENT PREPARATION OF DOLASTATIN AND AURISTATIN ANALOGS THROUGH A COMMON INTERMEDIATE

-

Paragraph 0116-0117, (2021/09/17)

Methods for making a dolastatin, auristatin or related compounds comprising the steps of providing a universal dolastatin core of Formula (I) reacting the C-terminal carboxylic acid group with an amine (A) to form an amide bond and reacting the N-terminal amine with a carboxylic acid (CA) to form an amide bond, wherein the steps can be performed in either order. Also provided are an isolated salt of the universal dolastatin core for use in preparation of dolastatins, auristatins and related compounds. Also provided are a number of intermediates and process steps which are useful for the preparation of high purity dolastatin core and high purity dolastatin and auristatin compounds.

Development of bifunctional anti-PD-L1 antibody MMAE conjugate with cytotoxicity and immunostimulation

Xiao, Dian,Luo, Longlong,Li, Jiaguo,Wang, Zhihong,Liu, Lianqi,Xie, Fei,Feng, Jiannan,Zhou, Xinbo

, (2021/09/27)

In recent years, tumor immunotherapy, especially the combination of PD1/PD-L1 inhibitors and chemotherapy, has developed rapidly. However, the systemic side effects induced by chemotherapy remain a crucial problem that needs to be addressed. Antibody drug conjugates (ADCs) are exceptional target-specific prodrugs that greatly improve the therapeutic window of chemotherapy drugs. Therefore, designing PD-L1-targeting ADCs is an interesting research project. In this study, we confirmed for the first time that the commercial anti-PD-L1 antibody Atezolizumab has better endocytosis efficiencies than Avelumab, and was more suitable for ADC design. Then, the most popular cytotoxic payload MMAE was conjugated to Atezolizumab via a classical dipeptide (valine-alanine) linker to generate a bifunctional PD-L1 ADC (ADC 3). An in vitro cytotoxicity test indicated the potent tumor cell inhibitory activity of ADC 3, with EC50 values of 9.75 nM to 11.94 nM. In addition, a co-culture of PBMCs in vitro proved that ADC 3 retained the immune activation effect of the Atezolizumab antibody. Moreover, ADC 3 exhibited a higher tumor inhibition rate and tumor regression rate in humanized immune system mice. To the best of our knowledge, this is the most active PD-L1-ADC reported thus far, which may promote the development of immunotherapy and novel ADCs.

ONE-POT PROCESS FOR PREPARING INTERMEDIATE OF ANTIBODY-DRUG CONJUGATE

-

Paragraph 0074; 0075; 0079-0081, (2021/04/02)

The present invention relates to a “one-pot process” for preparing intermediate of antibody-drug conjugate. The preparation process provided by the present invention is simple in operation, and needs no such steps like concentration, washing and filtratio

PROCESS FOR THE PREPARATION OF DRUG LINKER COMPOUNDS

-

Paragraph 0118, (2019/06/17)

This disclosure generally relates to novel processes for the preparation of drug linker compounds and compositions comprising such drug linker compounds. The presently disclosed methods for synthesizing Fmoc-Val-Cit-PABOH and related compounds have also been found to minimize formation of diastereomeric impurities.

An antibody-coupled drug targeting on EGFR, a preparation method thereof, and uses thereof

-

Paragraph 0051; 0071; 0072; 0073, (2019/01/24)

The invention discloses an antibody coupling drug targeting on EGFR, a preparation method thereof and uses thereof. The antibody-conjugated drug targeting EGFR is named LR004-VC-MMAE consisting of anantibody, a cytotoxic drug and a linker, wherein the antibody drug conjugate has a structure represented by the formula I, wherein mAb is an LR004 monoclonal antibody, n=2-8. The novel antibody-conjugated drug LR004-VC-MMAE can not only target EGFR antigen, but also has strong cytotoxicity to tumor cells. Compared with LR004 itself, it did not affect the affinity, endocytosis and targeting of theantibody, and better retained its biological function. Compared to LR004, the antitumor effect of LR004-VC-MMAE antibody-conjugated drug is significantly improved, and the tumor disappeared. Comparedto LR004, LR004-VC-MMAE antibody-conjugated total antibody showed longer half-life, slower clearance rate, lower concentration of free MMAE in plasma, shorter half-life and faster clearance rate, which is conducive to reduce toxicity.

Process route upstream and downstream products

Process route

6-maleimidohexanoic acid N-hydroxylsuccinimide ester
55750-63-5

6-maleimidohexanoic acid N-hydroxylsuccinimide ester

MMAE-PABA-Val-Cit-NH<sub>2</sub>

MMAE-PABA-Val-Cit-NH2

MMAE-PABA-Val-Cit-MI
646502-53-6

MMAE-PABA-Val-Cit-MI

Conditions
Conditions Yield
With benzotriazol-1-ol; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 4h;
46%
(1S,2R)-(+)-norphedrine
37577-28-9,58550-13-3,757124-50-8

(1S,2R)-(+)-norphedrine

4-((S)-2-((S)-2-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamido)-3-methylbutanamido)-5-ureidopentanamido)benzyl((S)-1-(((S)-1-(((3R,4S,5S)-1-((S)-2-((1R,2R)-3-(((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-yl)-3-methoxy-5-methyl-1-oxoheptan-4-yl)(methyl)amino)-3-methyl-1-oxobutan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)(methyl)carbamate
646502-53-6

4-((S)-2-((S)-2-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamido)-3-methylbutanamido)-5-ureidopentanamido)benzyl((S)-1-(((S)-1-(((3R,4S,5S)-1-((S)-2-((1R,2R)-3-(((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-yl)-3-methoxy-5-methyl-1-oxoheptan-4-yl)(methyl)amino)-3-methyl-1-oxobutan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)(methyl)carbamate

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: N,N-dimethyl-formamide / 20 °C
2: trifluoroacetic acid / dichloromethane / 20 °C / Cooling with ice
3: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide; dichloromethane / 20 °C
4: diethylamine / dichloromethane / 20 °C
5: benzotriazol-1-ol; pyridine / N,N-dimethyl-formamide / 20 °C
With pyridine; benzotriazol-1-ol; diethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; N,N-dimethyl-formamide;
N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-N<sup>5</sup>-carbamoyl-N[4-({[(4-nitrophenoxy)carbonyl]oxy}methyl)phenyl]-L-ornithinamide
159857-81-5

N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-N5-carbamoyl-N[4-({[(4-nitrophenoxy)carbonyl]oxy}methyl)phenyl]-L-ornithinamide

4-((S)-2-((S)-2-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamido)-3-methylbutanamido)-5-ureidopentanamido)benzyl((S)-1-(((S)-1-(((3R,4S,5S)-1-((S)-2-((1R,2R)-3-(((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-yl)-3-methoxy-5-methyl-1-oxoheptan-4-yl)(methyl)amino)-3-methyl-1-oxobutan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)(methyl)carbamate
646502-53-6

4-((S)-2-((S)-2-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamido)-3-methylbutanamido)-5-ureidopentanamido)benzyl((S)-1-(((S)-1-(((3R,4S,5S)-1-((S)-2-((1R,2R)-3-(((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-yl)-3-methoxy-5-methyl-1-oxoheptan-4-yl)(methyl)amino)-3-methyl-1-oxobutan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)(methyl)carbamate

Conditions
Conditions Yield
With 2,6-dimethylpyridine; 2-hydroxy-pyridine N-oxide; In N,N-dimethyl-formamide; at 20 ℃;
98%
With pyridine; benzotriazol-1-ol; In N,N-dimethyl-formamide; at 20 ℃; for 24h;
71%
With 2,6-dimethylpyridine; benzotriazol-1-ol; In N,N-dimethyl acetamide; at 40 ℃;
65%
With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃;
64%
With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃;
61%
N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-N5-carbamoyl-N[4-({[(4-nitrophenoxy)carbonyl]oxy}methyl)phenyl]-L-ornithinamide; With benzotriazol-1-ol; In N,N-dimethyl-formamide; at 20 ℃;
[3H]-Vedotin; With pyridine; N-ethyl-N,N-diisopropylamine; at 20 ℃; for 48h;
42%
With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 48h;
42%
With pyridine; benzotriazol-1-ol; In N,N-dimethyl-formamide; for 24h;
N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-N5-carbamoyl-N[4-({[(4-nitrophenoxy)carbonyl]oxy}methyl)phenyl]-L-ornithinamide; [3H]-Vedotin; With 1-hydroxy-7-aza-benzotriazole; In N,N-dimethyl-formamide; at 20 ℃; for 0.0833333h; Inert atmosphere;
With N-ethyl-N,N-diisopropylamine; at 40 - 50 ℃; for 20.5h;
10.7 g
With pyridine; benzotriazol-1-ol; In N,N-dimethyl-formamide; at 20 ℃;
With pyridine; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;
214 mg
N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-N<sup>5</sup>-carbamoyl-N[4-({[(4-nitrophenoxy)carbonyl]oxy}methyl)phenyl]-L-ornithinamide
159857-81-5

N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-N5-carbamoyl-N[4-({[(4-nitrophenoxy)carbonyl]oxy}methyl)phenyl]-L-ornithinamide

N-phenyl maleimide monomethyl-auristatin-E
1057314-02-9

N-phenyl maleimide monomethyl-auristatin-E

C<sub>68</sub>H<sub>105</sub>N<sub>11</sub>O<sub>15</sub>
646502-53-6

C68H105N11O15

Conditions
Conditions Yield
With pyridine; benzotriazol-1-ol; In N,N-dimethyl-formamide; at 20 ℃; for 24h;
71%
C<sub>35</sub>H<sub>43</sub>N<sub>7</sub>O<sub>11</sub>

C35H43N7O11

C<sub>68</sub>H<sub>105</sub>N<sub>11</sub>O<sub>15</sub>
646502-53-6

C68H105N11O15

Conditions
Conditions Yield
With pyridine; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 48h;
42%
monomethylauristatin E

monomethylauristatin E

4-((S)-2-((S)-2-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamido)-3-methylbutanamido)-5-ureidopentanamido)benzyl((S)-1-(((S)-1-(((3R,4S,5S)-1-((S)-2-((1R,2R)-3-(((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-yl)-3-methoxy-5-methyl-1-oxoheptan-4-yl)(methyl)amino)-3-methyl-1-oxobutan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)(methyl)carbamate
646502-53-6

4-((S)-2-((S)-2-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamido)-3-methylbutanamido)-5-ureidopentanamido)benzyl((S)-1-(((S)-1-(((3R,4S,5S)-1-((S)-2-((1R,2R)-3-(((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-yl)-3-methoxy-5-methyl-1-oxoheptan-4-yl)(methyl)amino)-3-methyl-1-oxobutan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)(methyl)carbamate

Conditions
Conditions Yield
With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃;
(S)-2-amino-N-((3R,4S,5S)-1-((S)-2-((1R,2R)-3-(((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-yl)-3-methoxy-5-methyl-1-oxoheptan-4-yl)-N,3-dimethylbutanamide

(S)-2-amino-N-((3R,4S,5S)-1-((S)-2-((1R,2R)-3-(((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-yl)-3-methoxy-5-methyl-1-oxoheptan-4-yl)-N,3-dimethylbutanamide

mc-Val-Cit-PAB-N-Me-Val-OH

mc-Val-Cit-PAB-N-Me-Val-OH

4-((S)-2-((S)-2-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamido)-3-methylbutanamido)-5-ureidopentanamido)benzyl((S)-1-(((S)-1-(((3R,4S,5S)-1-((S)-2-((1R,2R)-3-(((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-yl)-3-methoxy-5-methyl-1-oxoheptan-4-yl)(methyl)amino)-3-methyl-1-oxobutan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)(methyl)carbamate
646502-53-6

4-((S)-2-((S)-2-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamido)-3-methylbutanamido)-5-ureidopentanamido)benzyl((S)-1-(((S)-1-(((3R,4S,5S)-1-((S)-2-((1R,2R)-3-(((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-yl)-3-methoxy-5-methyl-1-oxoheptan-4-yl)(methyl)amino)-3-methyl-1-oxobutan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)(methyl)carbamate

Conditions
Conditions Yield
With 2,6-dimethylpyridine; HATU; In N,N-dimethyl-formamide;
20%
N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-N<sup>5</sup>-carbamoyl-N[4-({[(4-nitrophenoxy)carbonyl]oxy}methyl)phenyl]-L-ornithinamide
159857-81-5

N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-N5-carbamoyl-N[4-({[(4-nitrophenoxy)carbonyl]oxy}methyl)phenyl]-L-ornithinamide

C<sub>68</sub>H<sub>105</sub>N<sub>11</sub>O<sub>15</sub>
646502-53-6

C68H105N11O15

Conditions
Conditions Yield
With pyridine; benzotriazol-1-ol; In N,N-dimethyl-formamide; for 24h;
(S)-2-((S)-2-((((9H-fluoren-9-yl)-methoxy)carbonyl)amino)-3-methylbutanamido)-5-ureidopentanoic acid
159858-21-6

(S)-2-((S)-2-((((9H-fluoren-9-yl)-methoxy)carbonyl)amino)-3-methylbutanamido)-5-ureidopentanoic acid

4-((S)-2-((S)-2-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamido)-3-methylbutanamido)-5-ureidopentanamido)benzyl((S)-1-(((S)-1-(((3R,4S,5S)-1-((S)-2-((1R,2R)-3-(((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-yl)-3-methoxy-5-methyl-1-oxoheptan-4-yl)(methyl)amino)-3-methyl-1-oxobutan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)(methyl)carbamate
646502-53-6

4-((S)-2-((S)-2-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamido)-3-methylbutanamido)-5-ureidopentanamido)benzyl((S)-1-(((S)-1-(((3R,4S,5S)-1-((S)-2-((1R,2R)-3-(((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-yl)-3-methoxy-5-methyl-1-oxoheptan-4-yl)(methyl)amino)-3-methyl-1-oxobutan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)(methyl)carbamate

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / dichloromethane; methanol / 36 h / 20 °C
2: piperidine / N,N-dimethyl-formamide / 2 h / 20 °C
3: N,N-dimethyl-formamide / 6 h / 20 °C
4: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 5 h / 20 °C
5: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C
With piperidine; benzotriazol-1-ol; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;
Multi-step reaction with 5 steps
1.1: N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / dichloromethane; methanol / 48 h / 20 °C / Darkness
2.1: diethylamine / 24 h / 20 °C
3.1: 1-methyl-pyrrolidin-2-one / 24 h / Heating
4.1: pyridine / dichloromethane / 3.17 h / 0 - 20 °C / Inert atmosphere
5.1: benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C
5.2: 48 h / 20 °C
With pyridine; benzotriazol-1-ol; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; diethylamine; In 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; N,N-dimethyl-formamide;
Multi-step reaction with 5 steps
1: N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / dichloromethane; methanol / 48 h / 20 °C / Darkness
2: diethylamine / 1-methyl-pyrrolidin-2-one / 24 h / 20 °C
3: 1-methyl-pyrrolidin-2-one / 24 h / 20 °C
4: pyridine / dichloromethane / 3.17 h / 0 - 20 °C / Inert atmosphere
5: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 48 h / 20 °C
With pyridine; benzotriazol-1-ol; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; diethylamine; N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; N,N-dimethyl-formamide;
Multi-step reaction with 5 steps
1: N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / dichloromethane; methanol / 20 °C / Darkness
2: diethylamine / N,N-dimethyl-formamide / 20 °C
3: N,N-dimethyl-formamide / 20 °C
4: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C
5: benzotriazol-1-ol; pyridine / N,N-dimethyl-formamide / 20 °C
With pyridine; benzotriazol-1-ol; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; diethylamine; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;
Multi-step reaction with 5 steps
1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / water; N,N-dimethyl-formamide; ethyl acetate / 0 - 5 °C
2: diethylamine / N,N-dimethyl-formamide / 20 °C
3: N,N-dimethyl-formamide / 20 - 30 °C
4: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 25 °C
5: 2,6-dimethylpyridine; benzotriazol-1-ol / N,N-dimethyl acetamide / 40 °C
With 2,6-dimethylpyridine; benzotriazol-1-ol; diethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl acetamide; water; ethyl acetate; N,N-dimethyl-formamide;
Multi-step reaction with 5 steps
1: N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / dichloromethane; methanol / 36 h / 20 °C / Darkness
2: piperidine / N,N-dimethyl-formamide / 2 h / 20 °C
3: N,N-dimethyl-formamide / 20 °C
4: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 5 h / 20 °C
5: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C
With piperidine; benzotriazol-1-ol; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;
(9H-fluorenyl)methyl ((S)-1-(((S)-1-(((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidovalerylamido-2-yl)amino))-3-methylbutyramido-2-yl)-carbamate
159858-22-7

(9H-fluorenyl)methyl ((S)-1-(((S)-1-(((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidovalerylamido-2-yl)amino))-3-methylbutyramido-2-yl)-carbamate

4-((S)-2-((S)-2-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamido)-3-methylbutanamido)-5-ureidopentanamido)benzyl((S)-1-(((S)-1-(((3R,4S,5S)-1-((S)-2-((1R,2R)-3-(((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-yl)-3-methoxy-5-methyl-1-oxoheptan-4-yl)(methyl)amino)-3-methyl-1-oxobutan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)(methyl)carbamate
646502-53-6

4-((S)-2-((S)-2-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamido)-3-methylbutanamido)-5-ureidopentanamido)benzyl((S)-1-(((S)-1-(((3R,4S,5S)-1-((S)-2-((1R,2R)-3-(((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-yl)-3-methoxy-5-methyl-1-oxoheptan-4-yl)(methyl)amino)-3-methyl-1-oxobutan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)(methyl)carbamate

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: piperidine / N,N-dimethyl-formamide / 2 h / 20 °C
2: N,N-dimethyl-formamide / 6 h / 20 °C
3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 5 h / 20 °C
4: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C
With piperidine; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;
Multi-step reaction with 4 steps
1.1: diethylamine / 24 h / 20 °C
2.1: 1-methyl-pyrrolidin-2-one / 24 h / Heating
3.1: pyridine / dichloromethane / 3.17 h / 0 - 20 °C / Inert atmosphere
4.1: benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C
4.2: 48 h / 20 °C
With pyridine; benzotriazol-1-ol; diethylamine; In 1-methyl-pyrrolidin-2-one; dichloromethane; N,N-dimethyl-formamide;
Multi-step reaction with 4 steps
1: diethylamine / 1-methyl-pyrrolidin-2-one / 24 h / 20 °C
2: 1-methyl-pyrrolidin-2-one / 24 h / 20 °C
3: pyridine / dichloromethane / 3.17 h / 0 - 20 °C / Inert atmosphere
4: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 48 h / 20 °C
With pyridine; benzotriazol-1-ol; diethylamine; N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; dichloromethane; N,N-dimethyl-formamide;
Multi-step reaction with 4 steps
1: diethylamine / N,N-dimethyl-formamide / 20 °C
2: N,N-dimethyl-formamide / 20 °C
3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C
4: benzotriazol-1-ol; pyridine / N,N-dimethyl-formamide / 20 °C
With pyridine; benzotriazol-1-ol; diethylamine; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;
Multi-step reaction with 4 steps
1: diethylamine / N,N-dimethyl-formamide / 20 °C
2: N,N-dimethyl-formamide / 20 - 30 °C
3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 25 °C
4: 2,6-dimethylpyridine; benzotriazol-1-ol / N,N-dimethyl acetamide / 40 °C
With 2,6-dimethylpyridine; benzotriazol-1-ol; diethylamine; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl acetamide; N,N-dimethyl-formamide;
Multi-step reaction with 4 steps
1: piperidine / N,N-dimethyl-formamide / 2 h / 20 °C
2: N,N-dimethyl-formamide / 20 °C
3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 5 h / 20 °C
4: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 °C
With piperidine; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;

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