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Structure of 279255-90-2

Chemical Structure| 279255-90-2

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Product Details of [ 279255-90-2 ]

CAS No. :279255-90-2
Formula : C14H17NO3
M.W : 247.29
SMILES Code : O=C(N1C=CC2=C1C=CC(CO)=C2)OC(C)(C)C
MDL No. :MFCD09834884
InChI Key :XIMLBZMOOXHPJQ-UHFFFAOYSA-N
Pubchem ID :21865484

Safety of [ 279255-90-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 279255-90-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 18
Num. arom. heavy atoms 9
Fraction Csp3 0.36
Num. rotatable bonds 4
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 70.27
TPSA ?

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

51.46 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.74
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

2.38
Log Po/w (WLOGP)?

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

2.76
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.

2.04
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

1.96
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.38

Water Solubility

Log S (ESOL):?

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

-2.98
Solubility 0.26 mg/ml ; 0.00105 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-3.1
Solubility 0.196 mg/ml ; 0.000791 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

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

-3.19
Solubility 0.159 mg/ml ; 0.000641 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

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

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.

-6.12 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.

0.55

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)

2.04

Application In Synthesis of [ 279255-90-2 ]

* 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 [ 279255-90-2 ]

[ 279255-90-2 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 15893-47-7 ]
  • [ 279256-09-6 ]
  • [ 279255-90-2 ]
  • [ 879887-21-5 ]
  • [ 879887-65-7 ]
YieldReaction ConditionsOperation in experiment
11%; 55%; 12% With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20℃; for 8h; D-Leucinamide (1.0 g, 6.0 mmol), 1-(t-butyloxycarbonyl)-5-formylindole (Example 1, 1.23 g, 5.0 mmol) and DCE (15 mL) were mixed at room temperature. Sodium triacetoxyborohydride (1.48 g, 7.0 mmol) was added in one portion with vigorous stirring. After 2 h, another portion (0.15 g, 0.7 mmol) was added and stirring was continued for an additional 6 h. The reaction mixture was diluted with a saturated NaHCO3 solution (10 mL). Three extractions with EtOAc, washing the combined organic layers with brine, drying over Na2SO4 and filtration provided a solution. Removal of solvent in vacuo afforded an oil. Column chromatography (DCM:MeOH:95:5) provided three fractions, after removal of solvent in vacuo: (1) 1-(t-Butyloxycarbonyl)-5-hydroxymethylindole (162 mg, 11% yield, Rf=0.5): 1H NMR (CDCl3, 300 MHz): 8.11 (d, 1H, J=8), 7.61 (d, 1H, J=2), 7.54 (s, 1H), 7.31 (dd, 1H, J=8,2), 6.55 (d, 1H, J=3), 4.75 (s, 2H), 1.69 (s, 9H); (2) 2R-bis-(1-t-butyloxycarbonylindol-5-ylmethyl)amino-4-methylpentanamide BMS594447 (382 mg, 12% yield, Rf=0.4): 1H NMR (CDCl3, 300 MHz): 8.1 (d, 2H, J=8), 7.61 (d, 2H, J=2), 7.52 (s, 2H), 7.31 (dd, 2H, J=8,2), 6.62 (m, 1H), 6.56 (d, 2H, J=4), 6.05 (br s, 1H), 3.85 (d, 2H, J=16), 3.66 (d, 2H, J=16), 3.35 (m, 1H), 1.69 (s, 18H), 0.96 (d, 3H, J=7), 0.87 (d, 3H, J=7); MS (ES+): 589.4 (C35H45N3O5) and (3) the title product (986 mg, 55% yield, Rf=0.3): 1H NMR (CDCl3, 300 MHz): 8.10 (d, 1H, J=8), 7.61 (d, 1H, J=2), 7.49 (d, 1H, J=1), 7.28-7.20 (m, 3H), 6.55 (d, 1H, J=4), 3.93 (d, 1H, J=16), 3.77 (d, 1H, J=16), 3.28-3.20 (m, 1H), 1.69 (s, 9H), 0.94 (d, 3H, J=7), 0.85 (d, 3H, J=7); MS (ES+): 360 (C20H30N3O3, M++H).
  • 2
  • ammonium chloride [ No CAS ]
  • [ 272438-11-6 ]
  • [ 279255-90-2 ]
YieldReaction ConditionsOperation in experiment
With diisobutylaluminium hydride; In tetrahydrofuran; methanol; water; toluene; Step 2 To a solution of N-tert-butoxycarbonylindole-5-carboxylic acid methyl ester (23.6 g, 85.7 mmol) in dry tetrahydrofuran (225 mL) at -78 C. was added 1.5 M DIBALH in toluene (171 mL, 257 mmol). After 2 h, the reaction mixture was quenched by the slow addition of methanol (45 mL), water (60 mL), and saturated aqueous NH4Cl (30 mL). The cold bath was removed and after stirring for an additional 1 h, the reaction mixture was filtered over Celite. The Celite cake was washed with tetrahydrofuran and the filtrate was concentrated to remove the more volatile tetrahydrofuran. The biphasic mixture was extracted with ethyl acetate. The combined organic layers were washed with water and the aqueous layer back extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated to afford N-tert-butoxycarbonylindol-5-yl methanol (21.2 g).
  • 3
  • [ 182319-85-3 ]
  • [ 279255-90-2 ]
  • [ 10465-81-3 ]
  • [ 279255-91-3 ]
YieldReaction ConditionsOperation in experiment
With tributylphosphine; In benzene; Step 4 To an ice-cooled mixture of 2(R)-(4-methoxybenzenesulfonylamino)-3-methylbutyric acid benzyl ester (5 g, 13.25 mmol) [prepared as described in Example 2 above], N-tert-butoxycarbonyl-5-indole methanol (3.8 g, 14.6 mmol) and tributylphosphine (3.6 mL, 14.6 mmol) in dry benzene (60 mL) was added [1,1'-azodicarbonyl]dipiperidine (3.68 g, 14.6 mmol). The reaction mixture was stirred overnight at room temperature and then chromatographed on a silica gel column eluding with (5-10%) ethyl acetate/hexanes to give of 2(R)-[(N-tert-butoxy-carbonylindol-5-ylmethyl)-(4-methoxybenzenesulfonyl)amino]-3-methylbutyric acid benzyl ester (6.5 g) as a white foamy semi-solid.
  • 4
  • [ 272438-11-6 ]
  • [ 279255-90-2 ]
YieldReaction ConditionsOperation in experiment
With ammonium chloride; diisobutylaluminium hydride; In tetrahydrofuran; methanol; water; ethyl acetate; toluene; Step 3 To a cooled solution (-78 C.) of methyl (N-tert-butoxycarbonyl)indole-5-carboxylate (7.6 g, 27.9 mmol) in dry tetrahydrofuran (75 mL) was added diisobutylaluminum hydride (57 mL, 1.5 M in toluene) via syringe over 5 min. After 1.5 h, the reaction mixture was quenched by careful addition of methanol (15 mL) and allowed to warm to room temperature over 45 min. Water (20 mL) and a saturated solution of ammonium chloride(10 mL) was added with vigorous stirring and the resultant inorganic precipitate was removed by filtration. The filtrate was condensed on the roto-evaporator and the residue was partitioned between a 1:1 mixture of ethyl acetate/water (160 mL). The ethyl acetate phase was washed with brine and the aqueous phases back extracted with ethyl acetate. The organic phase was combined, dried with magnesium sulfate, filtered and concentrated to provide (N-tert-butoxycarbonyl)indole-5-methanol (7.35 g) as a semi-viscous yellow oil which was used in the next step without further purification.
  • 5
  • [ 279255-90-2 ]
  • [ 279256-09-6 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; Step 3 To a solution of <strong>[279255-90-2]N-tert-butoxycarbonylindol-5-yl methanol</strong> (2.56 g, 10.35 mmol) in dry methylene chloride (60 mL) was added manganese oxide (9 g, 103.5 mmol). The reaction mixture was stirred for 3 h at room temperature and then heated at reflux. After 3 h, the heterogeneous slurry was filtered through Celite and concentrated to afford N-tert-butoxycarbonyl-5-formylindole (2.5 g).
With manganese(IV) oxide; In dichloromethane; at 40℃; for 25h; A solution of tert-butyl 5-([tert-butyl(dimethyl)silyl]oxy}methyl)-1H-indole-1- carboxylate (1-6, 13.0 g, 36.0 mmol, 1 equiv) and triethylamine trihydrofluoride (5.86 mL, 36.0 ralphamol, 1.00 equiv) in acetonitrile (150 mL) was stirred at 23 C for 20 h. The reaction mixture was concentrated, and the residue was partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate (2 x 200 mL). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography (hexanes initially, grading to 60% EtOAc in hexanes) to provide the intermediate alcohol. A mixture of the alcohol and manganese (IV) oxide (6.25 g, 71.9 mmol, 2.00 equiv) in dichloromethane (200 mL) was heated at 40 C for 20 h. Additional manganese(IV) oxide (3.13 g, 36.0 mmol, 1.00 equiv) was added and heating was continued for 5 h. The solids were filtered and washed with dichloromethane (3 x 100 mL). The combined filtrate EPO <DP n="69"/>was concentrated to give tert-butyl 5-formyl-1H-indole-1-carboxylate (5-1) as a colorless oil. 1H NMR (300 MHz, CDCl3) delta 10.07 (s, 1H), 8.29 (d, 1H, J = 8.8 Hz), 8.10 (d, 1H, J = 1.6 Hz), 7.86 (dd, 1H, J = 8.8, 1.8 Hz), 7.69 (d, 1H, J = 4.0 Hz), 6.70 (dd, 1H, J = 3.7, 0.6 Hz), 1.70 (s, 9H). LRMS m/z (M+H- CH3) 231.2 found, 231.1 required.
  • 6
  • [ 335649-83-7 ]
  • [ 279255-90-2 ]
YieldReaction ConditionsOperation in experiment
With triethylamine tris(hydrogen fluoride); In acetonitrile; at 23℃; for 20h; A solution of tert-butyl 5-([tert-butyl(dimethyl)silyl]oxy}methyl)-1H-indole-1- carboxylate (1-6, 13.0 g, 36.0 mmol, 1 equiv) and triethylamine trihydrofluoride (5.86 mL, 36.0 ralphamol, 1.00 equiv) in acetonitrile (150 mL) was stirred at 23 C for 20 h. The reaction mixture was concentrated, and the residue was partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate (2 x 200 mL). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography (hexanes initially, grading to 60% EtOAc in hexanes) to provide the intermediate alcohol. A mixture of the alcohol and manganese (IV) oxide (6.25 g, 71.9 mmol, 2.00 equiv) in dichloromethane (200 mL) was heated at 40 C for 20 h. Additional manganese(IV) oxide (3.13 g, 36.0 mmol, 1.00 equiv) was added and heating was continued for 5 h. The solids were filtered and washed with dichloromethane (3 x 100 mL). The combined filtrate EPO <DP n="69"/>was concentrated to give tert-butyl 5-formyl-1H-indole-1-carboxylate (5-1) as a colorless oil. 1H NMR (300 MHz, CDCl3) delta 10.07 (s, 1H), 8.29 (d, 1H, J = 8.8 Hz), 8.10 (d, 1H, J = 1.6 Hz), 7.86 (dd, 1H, J = 8.8, 1.8 Hz), 7.69 (d, 1H, J = 4.0 Hz), 6.70 (dd, 1H, J = 3.7, 0.6 Hz), 1.70 (s, 9H). LRMS m/z (M+H- CH3) 231.2 found, 231.1 required.
  • 7
  • [ 279255-90-2 ]
  • [ 442685-53-2 ]
YieldReaction ConditionsOperation in experiment
93% With phosphorus tribromide; In diethyl ether; dichloromethane; for 0.666667h; To an ice-cold solution OF 5-HYDROXYMETHYLINDOLE-1-CARBAMIC acid tert-butyl ester (0.51 g, 2.1 mmol) in 4: 1 ET2O/CH2CL2 (4 ML) was added PBr3 (0.2 mL, 2.2 mmol), and the reaction mixture was stirred for 40 min. The reaction mixture was diluted with CH2C12, washed a saturated solution OF NAHC03 (3 x 10 mL), dried (NA2SO4), filtered, and the solvent was removed under reduced pressure to provide 5-BROMOMETHYL-INDOLE-1- carbamic acid tert-butyl ester as a yellow solid (0.59 g, 93%). IH NMR (300 MHz, CDC13) 8 8.07 (d, J= 9 Hz, 1H), 7.68-7. 62 (m, 2H), 7.33 (d, 7= 9 Hz, 1H), 6.60 (s, 1H), 4.68 (s, 2H), 1.67 (s, 9H).
  • 8
  • 5-(carboxymethyl)-indole-1-carbamic acid tert-butyl ester [ No CAS ]
  • [ 279255-90-2 ]
YieldReaction ConditionsOperation in experiment
68% With diisobutylaluminium hydride; In tetrahydrofuran; at -78℃; for 2.5h; To a-78C solution of 5-(carboxymethyl)i-indole-1-carbamic acid tert-butyl ester (10. 8 g, 39 mmol) in THF (180 ML) was added DIBAL (127 ML of a 1 M solution in THF, 127 mmol), and the reaction mixture was stirred for 2.5 h. The reaction was quenched with 1: 1 1 N HCI/MeOH (100 mL), the reaction mixture was warmed to room temperature, diluted with CH2Cl2 (100 mL), and separated. The organic solution was washed with saturated Rochelle salt, dried (NA2S04), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 1: 1 EtOAc/hexanes) provided 5-hydroxymethylindole-1-carbamic acid tert-butyl ester as a yellow oil (6.5 g, 68%) :H NMR (300 MHz, CDC) 8 8.07 (d, J = 9 Hz, 1H), 7.59 (d, J = 6 Hz, 1H), 7.54 (s, 1H), 7.28 (d, J = 9 Hz, 1H), 6.58 (D, J = 6 Hz, 1H), 4.73 (s, 2H), 1.97 (s, 9H).
  • 9
  • [ 279256-09-6 ]
  • [ 279255-90-2 ]
YieldReaction ConditionsOperation in experiment
83% With methanol; sodium tetrahydroborate; at 0 - 20℃; for 3h; To a solution of tert-butyl 5-formyl-1H-indo . g, 12.23 mmol) in methanol (30 mL) was added sodium tetrahydroborate (0.463 g, 12.23 mmol) at 0 C. The reaction mixture was stirred at 0 C for 3 hours then overnight at room temperature. The resulting solution was diluted with water (40 mL), then extracted with ethyl acetate (3 x 30 mL). The organic layers were combined, washed with aqueous sodium carbonate and brine, dried and concentrated under vacuum to afford tert-butyl 5-(hydroxymethyl)-1H-indole-1- carboxylate (2.5 g, 10.11 mmol, 83% yield) as a yellow oil. LCMS m/z = 270.3 [M+Na]+.
  • 10
  • [ 279255-90-2 ]
  • tert-butyl 5-((1S,2S,3R)-2-(hydroxymethyl)-2-methyl-3-(4-methylbenzyl)cyclopropyl)-1H-indole-1-carboxylate [ No CAS ]
  • 11
  • [ 279255-90-2 ]
  • tert-butyl 5-((1S,2S,3R)-2-(hydroxymethyl)-2-methyl-3-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)cyclopropyl)-1H-indole-1-carboxylate [ No CAS ]
  • 12
  • [ 279255-90-2 ]
  • [ 1838-94-4 ]
  • tert-butyl 5-((1R,2R)-1-hydroxy-2-(hydroxymethyl)-2-methylbut-3-en-1-yl)-1H-indole-1-carboxylate [ No CAS ]
  • tert-butyl 5-((1S,2S)-1-hydroxy-2-(hydroxymethyl)-2-methylbut-3-en-1-yl)-1H-indole-1-carboxylate [ No CAS ]
  • 13
  • [ 279255-90-2 ]
  • 2-chloro-4-ethyl-6-(4-(pyrrolidin-1-yl)piperidin-1-yl)pyridine-3,5-dicarbonitrile [ No CAS ]
  • tert-butyl 5-(((3,5-dicyano-4-ethyl-6-(4-(pyrrolidin-1-yl)piperidin-1-yl)pyridin-2-yl)thio)methyl)-1H-indole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
340 mg To a solution of tert-butyl 5-(h g, 11.32 mmol), triethylamine (1.719 g, 16.98 mmol) in dichloromethane (30 mL) was added dropwise methanesulfonyl chloride (1.297 g, 11.32 mmol) at 0 C. The reaction mixture was stirred for 3 hours at room temperature. The resulting solution was diluted with water (20 mL), extracted with ethyl acetate (3 x 15 mL). The organic layers were combined, washed with aqueous sodium carbonate and brine, dried and concentrated under vacuum to afford a yellow oil (3.1 g). To a solution of 2-chloro-4-ethyl-6-(4-(pyrrolidin-1-yl)piperidin-1- yl)pyridine-3,5-dicarbonitrile (620 mg, 1.80 mmol) in N,N-dimethylformamide (15 mL) was added potassium ethanethioate (247 mg, 2.16 mmol). After the reaction mixture stirring 30 minutes at room temperature the yellow oil above (645 mg) and triethylamine (456 mg, 4.51 mmol) were added to the reaction, and the reaction mixture was stirred overnight at room temperature. Water (20 mL) was added and the resulting solution was extracted with ethyl acetate (3 x 20 mL). The organic layers were combined, washed with aqueous sodium carbonate and brine, dried, filtered, and concentrated under vacuum. The residue was purified on a silica gel column (eluted with ethyl MeOH/DCM 1/20) to afford tert-butyl 5- (((3,5-dicyano-4-ethyl-6-(4-(pyrrolidin-1-yl)piperidin-1-yl)pyridin-2-yl)thio)methyl)-1H- indole-1-carboxylate (340 mg, 0.60 mmol) as a yellow solid. LCMS m/z = 571.4 [M+H]+.
  • 14
  • [ 279255-90-2 ]
  • 2-chloro-4-ethyl-6-(4-(pyrrolidin-1-yl)piperidin-1-yl)pyridine-3,5-dicarbonitrile [ No CAS ]
  • 2-(((1H-indol-5-yl)methyl)thio)-4-ethyl-6-(4-(pyrrolidin-1-yl)piperidin-1-yl)pyridine-3,5-dicarbonitrile [ No CAS ]
  • 15
  • [ 24424-99-5 ]
  • [ 279255-90-2 ]
  • 16
  • [ 33140-84-0 ]
  • [ 279255-90-2 ]
 

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Technical Information

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