27018-76-4|1-Benzyl-1H-indole-3-carboxylic acid| Ambeed

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Quality Control of [ 27018-76-4 ] Purity: 95% SDS Specification

COA

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Product Details of [ 27018-76-4 ]

CAS No. :	27018-76-4
Formula :	C₁₆H₁₃NO₂
M.W :	251.28
SMILES Code :	O=C(C1=CN(CC2=CC=CC=C2)C3=C1C=CC=C3)O
MDL No. :	MFCD00057094
InChI Key :	LVYDDRHDOKXFMW-UHFFFAOYSA-N
Pubchem ID :	33671

Safety of [ 27018-76-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Computational Chemistry of [ 27018-76-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	19
Num. arom. heavy atoms	15
Fraction Csp3	0.06
Num. rotatable bonds	3
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	74.65
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	42.23 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.05
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.59
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.39
Log P_o/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.	2.76
Log P_o/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	2.8
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.92

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.05
Solubility	0.0226 mg/ml ; 0.00009 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-4.16
Solubility	0.0172 mg/ml ; 0.0000686 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	-4.76
Solubility	0.00439 mg/ml ; 0.0000175 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	Yes
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	Yes
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	Yes
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.	-5.28 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	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.56

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)	1.67

Application In Synthesis of [ 27018-76-4 ]

* 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 [ 27018-76-4 ]

[ 27018-76-4 ] Synthesis Path-Downstream 1~35

1
[ 1217-89-6 ]
[ 105-39-5 ]
[ 121195-60-6 ]
[ 27018-76-4 ]

References: [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1905 - 1909.
[2]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1905 - 1909.

2
[ 10511-51-0 ]
[ 27018-76-4 ]

References: [1]Journal of the Chilean Chemical Society,2011,vol. 56,p. 866 - 869.
[2]Archiv der Pharmazie,1984,vol. 317,p. 847 - 851.
[3]Organic Letters,2019,vol. 21,p. 2048 - 2051.

3
[ 141943-02-4 ]
[ 27018-76-4 ]

References: [1]Tetrahedron Letters,1992,vol. 33,p. 2299 - 2302.

4
[ 109-01-3 ]
[ 27018-76-4 ]
(1-benzyl-1H-indol-3-yl)-(4-methyl-piperazin-1-yl)-methanone [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,1999,vol. 34,p. 93 - 105.

5
[ 27578-60-5 ]
[ 27018-76-4 ]
1-benzyl-1H-indole-3-carboxylic acid (2-piperidin-1-yl-ethyl)-amide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,1999,vol. 34,p. 93 - 105.

6
[ 934-98-5 ]
[ 27018-76-4 ]
1-benzyl-1H-indole-3-carboxylic acid [2-(4-methyl-piperazin-1-yl)-ethyl]-amide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,1999,vol. 34,p. 93 - 105.

7
[ 2759-28-6 ]
[ 27018-76-4 ]
N-(1-benzyl-3-indolecarbonyl)-4-benzylpiperazine [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,1999,vol. 34,p. 93 - 105.

8
[ 27018-76-4 ]
[ 4553-21-3 ]
1-benzyl-1H-indole-3-carboxylic acid [2-(4-benzyl-piperazin-1-yl)-ethyl]-amide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,1999,vol. 34,p. 93 - 105.

9
[ 27018-76-4 ]
[ 108-00-9 ]
N-(1-benzyl-3-indolecarbonyl)-2-dimethylaminoethylamine [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,1999,vol. 34,p. 93 - 105.

10
[ 27018-76-4 ]
[ 313350-41-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With oxalyl dichloride; In dichloromethane; at 20℃; for 3h;	Oxalyl chloride (5.1 mL, 58.5mmol) was added under nitrogen to a solution of l-benzylindole-3-carboxylic acid (3.00 g, 11.9 mmol) in 200 mL of methylene chloride at room temperature. After the addition the reaction was allowed to stir at room temperature for 3 h. The solvent and excess oxalyl chloride were removed under reduced pressure. To remove any residual oxalyl chloride the residue was taken up in benzene and then concentrated under reduced pressure to give l-benzl-lH-indole-3-carbiB.ipllhl6MSpBlig;,''9PAf U 'a^white solid that was used in the next step without additional purification.
	With oxalyl dichloride; In dichloromethane; at 20℃; for 2.66667h;	[0138] Example 10: Synthesis of 1-BENZYL-N-[3 -BROMO-4 -(LH-TETRAAZOL-5- YLMETHOXY)-1, 1 -BIPHENYL-4-YL] METHYL}-N-METHYL-LH-INDOLE-3-CARBOXAMIDE. [0139] STEP 1 : 1-BENZYL-LH-INDOLE-3-CARBONYLCHLORIDE. OXALYLCHLORIDE (7. 1 mL, 81. 4 mmol) was added under nitrogen dropwise over 10 minutes to a suspension of 1-BENZYL-LH- indole-3-carboxylic acid (4. 10G, 16.3 mmol) in 200 ML of methylene chloride at room temperature. When the oxalyl chloride was added there was an immediate evolution of gas and within 30 minutes all of the solid had dissolved. After the addition of the oxalyl chloride the reaction was stirred at room temperature for 2 h. The solvent and excess oxalyl chloride were removed under reduced pressure. The residue was taken up in benzene and then concentrated to dryness under reduced pressure to give L-BENZYL-LH-INDOLE-3-CARBONYL chloride, which was used in the following reaction without purification.

References: [1]Patent: WO2006/23865,2006,A1 .Location in patent: Page/Page column 38-39.
[2]European Journal of Medicinal Chemistry,1999,vol. 34,p. 93 - 105.
[3]Patent: WO2005/30702,2005,A1 .Location in patent: Page/Page column 54.
[4]Journal of the Chinese Chemical Society,2008,vol. 55,p. 1160 - 1165.
[5]Tetrahedron Letters,2014,vol. 55,p. 7114 - 7117.
[6]Journal of Medicinal Chemistry,2015,vol. 58,p. 785 - 800.
[7]Organic Letters,2019,vol. 21,p. 2048 - 2051.

12
[ 96-50-4 ]
[ 27018-76-4 ]
1-benzyl-1H-indole-3-carboxylic acid thiazol-2-ylamide [ No CAS ]

References: [1]Pharmazie,2002,vol. 57,p. 238 - 242.

13
[ 6298-19-7 ]
[ 27018-76-4 ]
1-benzyl-1H-indole-3-carboxylic acid (2-chloro-pyridin-3-yl)-amide [ No CAS ]

References: [1]Pharmazie,2002,vol. 57,p. 238 - 242.

14
[ 27018-76-4 ]
[ 62-53-3 ]
1-benzyl-N-phenyl-1H-indole-3-carboxamide [ No CAS ]

References: [1]Pharmazie,2002,vol. 57,p. 238 - 242.

15
[ 155134-26-2 ]
[ 27018-76-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium hydroxide; In tetrahydrofuran;	(Step 2) Synthesis of 1-benzylindole-3-carboxylic acid In THF (15 ml) was dissolved methyl 1-benzylindole-3-carboxylate (606.1 mg, 2.284 mmol). To the resulting solution was added 0.25N NaOH (8.0 ml) and the mixture was stirred at 70ØC for 18 hours. After the reaction mixture was cooled to room temperature, the solvent was distilled off under reduced pressure. The residue thus obtained was acidified with 1N HCl (5.5 ml). The crystals thus precipitated were collected by filtration under reduced pressure, washed with water and dried under reduced pressure to give 1-benzylindole-3-carboxylic acid (100%) as a light pink amorphous substance. 1H-NMR (DMSO-d6) delta: 5.49 (2H, s), 7.14-7.38 (7H, m), 7.52 (1H, m), 8.00 (1H, m), 8.21 (1H, s), 12.01 (1H, br s).

References: [1]Patent: EP1346982,2003,A1 .
[2]Pharmazie,2002,vol. 57,p. 238 - 242.
[3]Patent: EP1532980,2005,A1 .Location in patent: Page/Page column 39; 41.
[4]Tetrahedron Letters,2014,vol. 55,p. 7114 - 7117.
[5]MedChemComm,2016,vol. 7,p. 1759 - 1767.

16
[ 39979-08-3 ]
[ 27018-76-4 ]
7-[(1-benzyl-1H-indole-3-carbonyl)-amino]-heptanoic acid methyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1897 - 1901.

17
[ 27018-76-4 ]
7-amino-heptanoic acid benzyloxy-amide [ No CAS ]
1-benzyl-1H-indole-3-carboxylic acid (6-benzyloxycarbamoyl-hexyl)-amide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1897 - 1901.

18
[ 27018-76-4 ]
[ 637767-83-0 ]
1-Benzyl-1H-indole-3-carboxylic acid ((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-piperidin-2-ylmethyl)-amide [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2003,vol. 42,p. 4661 - 4664.

19
[ 771-61-9 ]
[ 27018-76-4 ]
[ 942157-12-2 ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 4181 - 4188.

20
[ 27018-76-4 ]
[ 942157-14-4 ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 4181 - 4188.

21
[ 27018-76-4 ]
4-(1-benzyl-1H-indol-3-yl)-N-tert-butyl-4-oxobutanamide [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 4181 - 4188.

22
[ 27018-76-4 ]
7-[(1-benzyl-1H-indole-3-carbonyl)-amino]-heptanoyl chloride [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1897 - 1901.

23
[ 27018-76-4 ]
7-[(1-benzyl-1H-indole-3-carbonyl)-amino]-heptanoic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1897 - 1901.

24
[ 27018-76-4 ]
1-benzyl-1H-indole-3-carboxylic acid (6-hydroxycarbamoyl-hexyl)-amide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1897 - 1901.
[2]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1897 - 1901.

25
[ 771-50-6 ]
[ 27018-76-4 ]

References: [1]Pharmazie,2002,vol. 57,p. 238 - 242.
[2]MedChemComm,2016,vol. 7,p. 1759 - 1767.

26
[ 942-24-5 ]
[ 27018-76-4 ]

References: [1]Pharmazie,2002,vol. 57,p. 238 - 242.
[2]Tetrahedron Letters,2014,vol. 55,p. 7114 - 7117.
[3]MedChemComm,2016,vol. 7,p. 1759 - 1767.

27
[ 100-39-0 ]
polymer-bound NMe₃⁽¹⁺⁾*SCN^(1-) [ No CAS ]
[ 27018-76-4 ]

References: [1]Pharmazie,2002,vol. 57,p. 238 - 242.

28
[ 27018-76-4 ]
1-(1-benzyl-3-indolecarbonyl)-4-(β-hydroxyethyl)piperazine [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,1999,vol. 34,p. 93 - 105.

29
[ 504-29-0 ]
[ 27018-76-4 ]
[ 852059-34-8 ]

References: [1]Patent: EP1532980,2005,A1 .Location in patent: Page/Page column 39; 41.

30
[ 27018-76-4 ]
[ 229007-09-4 ]
[ 874889-01-7 ]

Yield	Reaction Conditions	Operation in experiment
71%		EDCI (0.33 mmol, 0.07 g) was added in one portion to a suspension of (4-amino-benzyl)-methyl-(tetrahydro-pyran-4-yl)-amine Compound Id (0.25 mmol, 0.06 g), 1-benzyl-lH-indole-3-carboxylic acid Compound 13a (0.22 mmol, 0.06 g) and HOBt (0.22 mmol, 0.03g) in DMF (5.0 mL) at 0C. The resulting suspension was warmed to r.t. and then a crystal ofDMAP and Et3N (0.65 mmol, 0.1 mL) was added and the reaction mixture was stirredovernight. The orange-yellow suspension was poured in'water and was extracted with EtOAc(25 mL). The organic layer was washed with water (2 X 20 mL) followed by 5% NaOHsolution (10 mL) and brine. The organic layer was separated, dried over Na2SO4 and filtered.The solvent was removed in vacua and the resulting residue was purified by preparative TLC(15:1 CH2Cl2/MeOH) to yield Compound 13b as a pale yellow solid (0.07 g, 71%). MS m/e454 (M*H, 100%).; lodomethane (0.5 mL) was added to a solution of Compound 13b (0.08 mmol, 0.04 g)in CH2C12 (1.0 mL) at r.t. The mixture was allowed to stand overnight and a yellow precipitatewas observed. The solvent was removed in vacua and the yellow solid was washed with Et2Oto obtain Compound 162 as a yellow solid (0.05 g, 84%). MS m/e 469 (M+H, 100%).
71%	With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 0 - 20℃;	EDCI (0.33 mmol, 0.07 g) was added in one portion to a suspension of (4-amino-benzyl)-methyl-(tetrahydro-pyran -4-yl)-amine Compound 1d (0.25 mmol, 0.06 g), <strong>[27018-76-4]1-benzyl-1H-indole-3-carboxylic acid</strong> Compound 13a (0.22 mmol, 0.06 g) and HOBt (0.22 mmol, 0.03 g) in DMF (5.0 mL) at 0 C. The resulting suspension was warmed to r.t. and then a crystal of DMAP and Et3N (0.65 mmol, 0.1 mL) was added and the reaction mixture was stirred overnight. The orange-yellow suspension was poured in water and was extracted with EtOAc (25 mL). The organic layer was washed with water (2×20 mL) followed by 5% NaOH solution (10 mL) and brine. The organic layer was separated, dried over Na2SO4 and filtered. The solvent was removed in vacuo and the resulting residue was purified by preparative TLC (15:1 CH2Cl2/MeOH) to yield Compound 13b as a pale yellow solid (0.07 g, 71%). MS m/e 454 (M+H, 100%).

References: [1]Patent: WO2006/12135,2006,A1 .Location in patent: Page/Page column 71-72.
[2]Patent: US2006/293379,2006,A1 .Location in patent: Page/Page column 79.

31
[ 79-37-8 ]
[ 27018-76-4 ]
[ 313350-41-3 ]

Yield	Reaction Conditions	Operation in experiment
	N,N-dimethyl-formamide; In dichloromethane;	Step 1 1-Benzyl-1H-indole-3-carbonyl chloride. A mixture of <strong>[27018-76-4]1-benzyl-1H-indole-3-carboxylic acid</strong> (3.36 g, 13.37 mmol), oxalyl chloride (5.83 mL, 66.85 mmol), 100 mL methylene chloride and a catalytic amount of DMF was stirred at room temperature under nitrogen for 18 h (overnight). The solvent was removed under reduced pressure. To remove excess oxalyl chloride benzene was added and the solvent removed under reduced pressure to give 1-benzyl-1H-indole-3-carbonyl chloride as a brown oil (13.37 mmol) which was immediately used in step 2 without additional purification.

References: [1]Patent: US2003/45560,2003,A1 .

32
[ 27018-76-4 ]
9,9,9-trifluoro-8-oxo-N-(4-pyridinyl)nonanamide [ No CAS ]
[ 436151-81-4 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 161 1-benzyl-N-(8-(methylamino)-7,8-dioxooctyl)-1H-indole-3-carboxamide The desired product was prepared by substituting Example 142F and 1-benzyl-3-indole carboxylic acid for 4-aminopyridine and Example 1B, respectively, in Example 6. MS (ESI(+)) m/e 420 (M+H)+; 1H NMR (DMSO-d6) delta8.53-8.46 (br m, 1H), 8.16-8.13 (m, 1H), 8.09 (s, 1H), 7.88-7.85 (br m, 1H), 7.50 (d, 1H), 7.36-7.22 (m, 5H), 7.20-7.09 (m, 2H), 5.45 (s, 2H), 3.26-3.19 (m, 2H), 2.80 (t, 2H), 2.64 (d, 3H), 1.56-1.46 (m, 4H), 1.35-1.28 (m, 4H).

References: [1]Patent: US2002/177594,2002,A1 .

33
[ 187947-61-1 ]
[ 27018-76-4 ]
[ 187945-09-1 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; In N,N-dimethyl-formamide;	EXAMPLE 6 To a stirring solution of (3S)-3-[(2S)-2-amino-5-benzyloxycarbonylpentanoyl]oxy-4-(6-ethyl-2-naphthyl)butanamide hydrochloride (0.20 g), <strong>[27018-76-4]1-benzylindole-3-carboxylic acid</strong> (105 mg) and HOBt (62 mg) in DMF (2 ml) was added WSCD (71 mg) at 0 C. After being stirred at room temperature overnight, the mixture was diluted with ethyl acetate and washed with 1N hydrochloric acid, aqueous ammonium chloride, aqueous sodium bicarbonate and brine, successively. The organic layer was dried over magnesium sulfate and concentrated in vacuo to give (3S)-3-[(2S)-2-(1-benzylindol-3-ylcarbonylamino)-5-benzyloxycarbonylpentanoyl]oxy-4-(6-ethyl-2-naphthyl)butanamide (0.26 g). NMR (CDCl3, delta): 8.20 (1H, s), 8.1 (2H, m), 7.1-7.8 (19H, m), 6.66 (1H, d, J=10Hz), 6.1 (1H, br s), 5.6 (1H, m), 5.34 (2H, s), 5.08 (2H, s), 4.7 (1H, m), 3.1 (2H, m), 2.74 (2H, q, J=7.5Hz), 2.1-2.6 (4H, m), 1.4-1.9 (4H, m), 1.28 (3H, t, J=7.5Hz) ESI-MS: 724 [M+H]

References: [1]Patent: US2002/19416,2002,A1 .

34
[ 79-37-8 ]
[ 27018-76-4 ]
[ 101349-30-8 ]
methyl 4-((1-benzyl-3-indolylcarbonyl)amino)-3-chlorophenylacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With triethylamine; In dichloromethane;	(Step 3) Synthesis of methyl 4-((1-benzyl-3-indolylcarbonyl)amino)-3-chlorophenylacetate To a solution of <strong>[27018-76-4]1-benzylindole-3-carboxylic acid</strong> (201.3 mg, 0.801 mmol) in methylene chloride (4.0 ml) was added oxalyl chloride (103.1 ael, 1.202 mmol) under stirring at -15ØC. The reaction mixture was stirred at room temperature for 2.5 hours and then, distilled under reduced pressure to remove the solvent. The residue was dissolved in methylene chloride (4.0 ml) and to the resulting solution were added a solution of methyl 3-chloro-4-aminophenylacetate (167.9 mg, 0.841 mmol) in methylene chloride (4.0 ml) and triethylamine (0.35 ml, 2.523 mmol) under stirring at room temperature. The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was distilled under reduced pressure to remove the solvent. The residue was diluted with chloroform, washed with 1N HCl dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent, whereby methyl 4-((1-benzyl-3-indolylcarbonyl)amino)-3-chlorophenylacetate (341.3 mg, 98%) was obtained. The compound was provided for the subsequent reaction without further purification. 1H-NMR (CDCl3) delta: 3.59 (2H, s), 3.71 (3H, s,), 5.38 (2H, s), 7.08-7.42 (10H, m), 7.87 (1H, s), 8.16 (1H, d, J=7.6Hz), 8.29 (1H, s), 8.58 (1H, d, J=8.0Hz).

References: [1]Patent: EP1346982,2003,A1 .

35
[ 100-39-0 ]
[ 27018-76-4 ]

Yield	Reaction Conditions	Operation in experiment
78%		1-benzyl-1H-indole-3-carboxylic acid To a stirred solution of 0.50 g (3.10 mmol) 1H-indole-3-carboxylic acid in 5 ml DMF was added 0.27 g (6.75 mmol) of NaH (60% in oil). The mixture was stirred at RT for 30 min. and then 0.39 ml (3.28 mmol) of benzyl bromid was added. The mixture was stirred an additional hour and then poured onto water and extracted with ethyl acetate. The combined organic phases were dried over Na2SO4 and concentrated in vacuo. Crystallization in Et2O afforded 0.61 g (78%) of 1-benzyl-1H-indole-3-carboxylic acid as a white solid. ES-MS m/e (%): 250 (M-H+).

References: [1]Patent: US2007/27173,2007,A1 .Location in patent: Page/Page column 35.
[2]Tetrahedron Letters,2014,vol. 55,p. 7114 - 7117.
[3]Tetrahedron,2016,vol. 72,p. 734 - 745.

Historical Records

Technical Information

• Arndt-Eistert Homologation • Hunsdiecker-Borodin Reaction • Passerini Reaction • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Carboxylic Acids • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Ugi Reaction

Related Functional Groups of
[ 27018-76-4 ]

Aryls

A198576 [4662-03-7]

2-(2-Phenyl-1H-indol-3-yl)acetic acid

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A292273 [945655-38-9]

Ethyl 6-amino-2-phenyl-1H-indole-3-carboxylate

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A525888 [886363-18-4]

4-(1H-Indol-5-yl)benzoic acid

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A255386 [72548-79-9]

3-(Pyrrolidin-1-yl)benzoic acid

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A290035 [1215494-12-4]

4-(Azetidin-1-yl)benzoic acid

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Carboxylic Acids

A449080 [727421-73-0]

1-Pentyl-1H-indole-3-carboxylic acid

Similarity: 0.94

A160093 [32387-21-6]

1-Methyl-1H-indole-3-carboxylic acid

Similarity: 0.92

A175020 [30448-16-9]

7-Methyl-1H-indole-3-carboxylic acid

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A243469 [209920-43-4]

6-Methyl-1H-indole-3-carboxylic acid

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A284593 [10242-02-1]

5-Methyl-1H-indole-3-carboxylic acid

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Related Parent Nucleus of
[ 27018-76-4 ]

Indoles

A449080 [727421-73-0]

1-Pentyl-1H-indole-3-carboxylic acid

Similarity: 0.94

A160093 [32387-21-6]

1-Methyl-1H-indole-3-carboxylic acid

Similarity: 0.92

A175020 [30448-16-9]

7-Methyl-1H-indole-3-carboxylic acid

Similarity: 0.88

A243469 [209920-43-4]

6-Methyl-1H-indole-3-carboxylic acid

Similarity: 0.88

A284593 [10242-02-1]

5-Methyl-1H-indole-3-carboxylic acid

Similarity: 0.87

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CAS No.: 27018-76-4

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