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Structure of 1408074-83-8

Chemical Structure| 1408074-83-8

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Product Details of [ 1408074-83-8 ]

CAS No. :1408074-83-8
Formula : C9H16F2N2O2
M.W : 222.23
SMILES Code : O=C(N1CC(F)(F)C(N)C1)OC(C)(C)C
MDL No. :MFCD23105898
InChI Key :DODJSPBKCAGGTQ-UHFFFAOYSA-N
Pubchem ID :72207756

Safety of [ 1408074-83-8 ]

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

Computational Chemistry of [ 1408074-83-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 0
Fraction Csp3 0.89
Num. rotatable bonds 3
Num. H-bond acceptors 5.0
Num. H-bond donors 1.0
Molar Refractivity 54.63
TPSA ?

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

55.56 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.13
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

0.68
Log Po/w (WLOGP)?

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

1.66
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.

0.86
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

0.51
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.17

Water Solubility

Log S (ESOL):?

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

-1.45
Solubility 7.92 mg/ml ; 0.0356 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.

-1.42
Solubility 8.38 mg/ml ; 0.0377 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

-1.19
Solubility 14.3 mg/ml ; 0.0644 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

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.

-7.17 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)

2.93

Application In Synthesis of [ 1408074-83-8 ]

* 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 [ 1408074-83-8 ]

[ 1408074-83-8 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 1610703-67-7 ]
  • [ 1408074-83-8 ]
  • [ 1610703-91-7 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In tert-butyl alcohol; at 20 - 90℃; for 120.0h; To a solution of tert-butyl 4-amino-3, 3-difluoropyrrolidine-l-carboxylate (880 mg, 4 mmol) in t-BuOH (5 mL) was added DIEA (0.7 mL, 4 mmol) and Intermediate IA (400 mg, 1.5 mmol) at RT. The mixture was heated to 90 °C and stirred at this temperature for 5 days. The solution was then cooled and the solvents were removed under reduced pressure. The residue obtained was purified by reverse-phase preparative HPLC (Column: Xbridge Prep C18 10 um OBD, 19 x 250 mm; Mobile phase: A: water (10 mM NH4HCO3), B: MeCN; Flow rate: 30 mL/min; UV detection: 214/254 nm) to afford tert-butyl 4-(9-ethyl-8-(2-methylpyrimidin-5-yl)-9H-purin-6- ylamino)-3,3-difluoropyrrolidine-l-carboxylate (1-21). 1H NMR (400 MHz, CD3OD) delta 9.22 - 9.10 (m, 2H), 8.39 (s, 1H), 5.52 - 5.43 (m, 1H), 4.41 (q, / = 7.2 Hz, 2H), 4.10 - 3.73 (m, 3H), 3.52 - 3.39 (m, 1H), 2.83 (s, 3H), 1.49 (s, 9H), 1.46 (t, / = 7.2 Hz, 3H). MS (ESI) calc'd for (C21H27F2N8O2) [M+H]+, 461 ; found, 461.
  • 2
  • [ 1648727-30-3 ]
  • [ 1408074-83-8 ]
  • 3
  • [ 203434-45-1 ]
  • [ 1408074-83-8 ]
  • 4
  • [ 1610703-68-8 ]
  • [ 1408074-83-8 ]
YieldReaction ConditionsOperation in experiment
With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 15.0h;Inert atmosphere; To a stirred solution of tert-butyl 4-azido-3, 3-difluoropyrrolidine-l-carboxylate (1.4 g, 5.6 mmol) in MeOH (10 mL) was added Pd/C (10percent by weight) (0.2 g, 10percent by weight, 0.188 mmol) at RT. The mixture was degassed with nitrogen, and subsequently the mixture was stirred under a balloon at RT for 15 h . The mixture was filtered through a pad of Celite and the filtrate was concentrated in vacuo to provide tert-butyl 4-amino-3, 3-difluoropyrrolidine-l-carboxylate. MS (ESI) calc'd for (C5H9F2N202) [M-tBu+2H]+, 167; found, 167.
With palladium on carbon; hydrogen; In ethanol; for 16.0h; A solution of tert-butyl 4-azido-3,3-difluoropyrrolidine-1-carboxylate (3.01 g, 12.1 mmol) in ethanol (300 mL) was degassed with nitrogen and 20percent Pd/C (300 mg) was added. The resulting mixture was stirred under hydrogen atmosphere (balloon) for 16 hr. The catalyst was removed by filtration. The filtrate was evaporated to give the title product as an oil (2.63 g, 98percent yield, >85percent purity). 1H NMR (400 MHz, chloroform-d) delta ppm 3.73-3.87 (m, 2H) 3.69 (d, J=10.64 Hz, 1H) 3.50-3.62 (m, 1H) 3.13 (d, J=6.85 Hz, 1H) 1.45-1.48 (m, 9H). 19F NMR (376 MHz, chloroform-d) delta ppm ?115.05-?110.78 (m, 1F) ?120.95-?117.90 (m, 1F). m/z (APCI+) for C9H16F2N2O2 123 (M+H)+
  • 5
  • [ 1434141-81-7 ]
  • [ 1408074-83-8 ]
  • 6
  • tert-butyl 3,3-difluoro-4-[(trifluoromethyl)sulfonyl]oxy}pyrrolidine-1-carboxylate [ No CAS ]
  • [ 1408074-83-8 ]
YieldReaction ConditionsOperation in experiment
99% With tetrabutylammoniun azide; In N,N-dimethyl-formamide; at 20℃; for 3.0h;Inert atmosphere; Cooling with ice; tert-butyl 3,3-difluoro-4-(trifluoromethylsulfonyloxy)pyrrolidine-1-carboxylate (1500 mg, 4.22 mmol), prepared following WO2017103611 example 160, was dissolved in DMF (20 mL) and cooled in an ice bath under N2 atmosphere. tetrabutylammonium azide (1200 mg, 4.22 mmol) in DMF (20 mL) was added slowly over 15 min via an addition funnel. The reaction mixture was stirred in the cold bath and allowed to warm to ambient temperature gradually and stirred for 3 h. The reaction was diluted with ethyl acetate (50 mL), washed with sat. aq. NaHCO3 (×2) and brine (×2). The organic phase was dried over a phase separator and purged with vacuum/N2 (3 times) followed by 10 the addition of palladium, 10 wt. % on carbon powder, dry (150 mg, 1.4 mmol).3 cycles vacuum/H2 were then performed and the reaction was left stirring at RT overnight under an atmosphere of hydrogen. The crude was filtered through a plug of CeliteTM and the solvent removed in vacuo. The product was purified by silica column chromatography using as eluting with 0-5% MeOH in DCM to afford [tert-butyl 4-amino-3,3-difluoropyrrolidine-1-carboxylate (934 mg, 4.2 mmol, 99% yield) ] as a 15 colourless oil. UPLC-MS (ES+, Method A), 1.04 min, m/z 167.0 [M-(tBu)+H]+
  • 7
  • [ 645-83-0 ]
  • [ 1408074-83-8 ]
  • tert-butyl 3,3-difluoro-4-[3-(methylsulfonyl)propanoyl]amino}pyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 2.0h;Inert atmosphere; To a reaction flask was added <strong>[1408074-83-8]tert-butyl 4-amino-3,3-difluoropyrrolidine-1-carboxylate</strong> (1.36 g, 6.12 mmol), 3-(methylsulfonyl)propanoic acid (1.02 g, 6.73 mmol, 1.1 mol eq), DCM (31 mL, 0.4 M), NMM (1.35 mL, 12.2 mmol, 2 mol eq), HOBt (1.31 g, 9.2 mmol, 1.5 mol eq) and EDC-HCl (1.85 g, 9.2 mmol, 1.5 mol eq). The resulting suspension was stirred at ambient temperature under a nitrogen atmosphere for 2 hr. The reaction was diluted with DCM (80 mL), washed with aqueous NaHCO3 (2×30 mL) and the organic layer was dried over Na2SO4 and evaporated to give a residue that was purified via silica flash chromatography eluting with gradients from 100percent heptane to 100percent ethyl acetate to give the title product as a white foamy solid (1.65 g, 76percent yield, >95percent purity). 1H NMR (400 MHz, chloroform-d) delta ppm 6.45 (br. s., 1H) 4.68-4.89 (m, 1H) 3.94 (dd, J=10.70, 8.62 Hz, 1H) 3.62-3.86 (m, 2H) 3.43 (t, J=7.15 Hz, 2H) 3.18 (br. s., 1H) 2.97 (s, 3H) 2.84 (td, J=7.15, 1.96 Hz, 2H) 1.47 (s, 9H). 19F NMR (376 MHz, chloroform-d) delta ppm ?112.79-?110.52 (m, 1F) ?114.51-?113.30 (m, 1F). m/z (APCI+) for C13H22F2N2O5S 257.1 (M+H)+
  • 8
  • [ 1408074-83-8 ]
  • 4-chloro-3-nitroquinoline-6-carbonitrile [ No CAS ]
  • tert-butyl 4-[(6-cyano-3-nitroquinolin-4-yl)amino]-3,3-difluoropyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 14.0h; tert-Butyl 4-am ino-3,3-difluoropyrrolidine-1 -carboxylate (prepared using themethod described by D. C. Behenna et al., in U.S. Published Patent Application 20150141402 Al, May 21, 2015; 2.30 g, 10.3 mmol) was dissolved in acetonitrile (20 mL). N,N-Diisopropylethylamine (2.01 g, 15.5 mmol) and C224 (3.04 g, 13.0 mmol) were added to this solution, and the reaction mixture was stirred for 14 hours at 20 °C. After removal of volatiles in vacuo, purification via silica gel chromatography (Gradient: 9percent to17percent tetrahydrofuran in petroleum ether) provided the product as a pale yellow solid.Yield: 3.20 g, 7.63 mmol, 74percent. H NMR (400 MHz, CDCI3) 9.52 (5, 1H), 9.21-9.04 (brm, 1H), 8.48 (br s, 1H), 8.20 (d, J=8.8 Hz, 1H), 8.00 (dd, J=8.6, 1.5 Hz, 1H), 4.88-4.74(m, 1H), 4.23 (br dd, J=9.7, 8.8 Hz, 1H), 4.05-3.89 (br m, 1H), 3.89-3.75 (m, 1H), 3.60(ddd, J=ii.4, 8.4, 1.3 Hz, 1H), 1.51 (5, 9H).
74% With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 14.0h; tert-Butyl 4-amino-3,3-difluoropyrrolidine-1 -carboxylate (prepared using the method described by D. C. Behenna et al., in U.S. Patent Application 2015 0141402 Al May 21 2015; 2.30 g, 10.3 mmol) was dissolved in acetonitrile (20 mL). N,N15 Diisopropylethylamine (2.01 g, 15.5 mmol) and CII (3.04 g, 13.0 mmol) were added tothis solution, and the reaction mixture was stirred for 14 hours at 20 °C. After removal of volatiles in vacuo, purification via silica gel chromatography (Gradient: 9percent to 17percent tetrahydrofuran in petroleum ether) provided the product as a pale yellow solid. Yield:3.20g, 7.63mmol, 74percent. H NMR(400MHz, CDCI3)E9.52(s, 1H), 9.21-9.04(brm,1 H), 8.48 (br s, 1 H), 8.20 (d, J=8.8 Hz, 1 H), 8.00 (dd, J=8.6, 1.5 Hz, 1 H), 4.88-4.74 (m,1 H), 4.23 (br dd, J=9.7, 8.8 Hz, 1 H), 4.05-3.89 (br m, 1 H), 3.89-3.75 (m, 1 H), 3.60 (ddd, J=ll.4, 8.4, 1.3 Hz, 1H), 1.51 (5, 9H).
  • 9
  • [ 1408074-83-8 ]
  • [ 99010-07-8 ]
  • tert-butyl 3,3-difluoro-4-[(6-fluoro-3-nitroquinolin-4-yl)amino]pyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 48.0h; To a 15°C solution of 4-chloro-6-fluoro-3-nitroquinoline (10.0 g, 44.1 mmol) inacetonitrile (50 mL) was added N,N-diisopropylethylamine (6.84 g, 52.9 mmol), followed by addition of <strong>[1408074-83-8]tert-butyl 4-amino-3,3-difluoropyrrolidine-1-carboxylate</strong> (prepared usingthe method described by D. C. Behenna et al., in U.S. Patent Application 2015 0141402 Al May 21 2015; 9.81 g, 44.1 mmol). The reaction mixture was stirred at 20 °C for 48 hours, whereupon it was concentrated in vacuo and purified via chromatography onsilica gel (Gradient: 9percent to 17percent tetrahydrofuran in petroleum ether) to afford the product as a pale yellow solid. Yield: 16.8 g, 40.7 mmol, 92percent. 1H NMR (400 MHz, CDCI3) 9.39(5, 1H), 8.87-8.69(brm, 1H), 8.13(dd, J=9.5, 5.5 Hz, 1H), 7.79-7.70(brd, J=8 Hz, 1H),7.63 (ddd, J=9.0, 7.5, 2.5 Hz, 1H), 4.87-4.71 (br m, 1H), 4.31 -4.09 (br m, 1H), 4.04-3.84 (br m, 1 H), 3.84-3.69 (m, 1 H), 3.63-3.51 (br m, 1 H), 1.50 (5, 9H).
  • 10
  • [ 1408074-83-8 ]
  • [ 39487-85-9 ]
  • tert-butyl 4-[(6-chloro-3-nitroquinolin-4-yl)amino]-3,3-difluoropyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 32.0h; To a solution of C7 (13.1 g, 53.9 mmol) in acetonitrile (60 mL) was added N,Ndiisopropylethylamine (11.3 mL, 64.9 mmol), followed by addition of a solution of tertbutyl 4-amino-3,3-difluoropyrrolidine-1 -carboxylate (prepared using the methoddescribed by D. C. Behenna et al., in U.S. Patent Application 2015 0141402 Al, May21 2015; 12.0 g, 54.0 mmol) in acetonitrile (5 mL). After the reaction mixture had beenstirred at 20 °C for 32 hours, it was diluted with water (100 mL). The resulting solid wascollected by filtration and purified via chromatography on silica gel (Gradient: 0percent to25percent tetrahydrofuran in petroleum ether), affording the product as a yellow solid. Yield:12.0 g, 28.0 mmol, 52percent. LCMS m/z 428.7 (chlorine isotope pattern observed) [M+H].1H NMR (400 MHz, CDCl3)9.4l (5, 1H), 8.91-8.78(brm, 1H), 8.08 (brs, 1H), 8.06(d, J=9.0 Hz, 1H), 7.79(dd, J=9.0, 2.0 Hz, 1H), 4.86-4.72 (brm, 1H), 4.30-4.12(brm, 1H), 4.03-3.86 (br m, 1 H), 3.86-3.71 (m, 1 H), 3.64-3.52 (br m, 1 H), 1.51 (5, 9H).
  • 11
  • [ 1408074-83-8 ]
  • 5-(4-amino-5-(trifluoromethyl)pyrrolo[2,1-f][1,2,4]triazin-7-yl)-2-methoxynicotinic acid [ No CAS ]
  • tert-butyl 4-(5-(4-amino-5-(trifluoromethyl)pyrrolo[2,1-f][1,2,4]triazin-7-yl)-2-methoxynicotinamido)-3,3-difluoropyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 23℃; for 2.0h; To a solution of 5-(4- amino-5-(trifluoromethyl)pyrrolo[2,1-f][1,2,4]triazin-7-yl)-2-methoxynicotinic acid (130 mg, 0.368 mmol), <strong>[1408074-83-8]tert-butyl 4-amino-3,3-difluoropyrrolidine-1-carboxylate</strong> (82 mg, 0.368 mmol) and DIPEA (0.193 mL, 1.104 mmol) in DMF (2 mL) was added BOP (195 mg, 0.442 mmol). The reaction mixture was stirred at 23 °C for 2 h. The reaction mixture was diluted with EtOAc (80 mL) which was washed with 10 percent LiCl solution (2 x 30 mL), brine (30 mL) and dried over anhydrous sodium sulfate. Filtration and concentration yielded tert-butyl 4-(5-(4-amino-5-(trifluoromethyl)pyrrolo[2,1-f][1,2,4]triazin-7-yl)-2- methoxynicotinamido)-3,3-difluoropyrrolidine-1-carboxylate (248 mg, 0.439 mmol, ~100 percent yield). (1207) MS ESI m/z 558.1 (M+H)+ (1208) 1H NMR (400 MHz, DMSO-d6) delta 8.94 (d, J=2.4 Hz, 1H), 8.69 (d, J=2.4 Hz, 1H), 8.65 (d, J=8.7 Hz, 1H), 8.18 (s, 1H), 7.63 (s, 1H), 5.14 - 4.94 (m, 1H), 4.03 (s, 3H), 3.90 - 3.47 (m, 4H), 1.43 (s, 9H).
 

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Pyrrolidines

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