1147422-00-1|tert-Butyl octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate| Ambeed

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 1147422-00-1 ] Purity: 95% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 1147422-00-1 ]

CAS No. :	1147422-00-1
Formula :	C₁₂H₂₂N₂O₂
M.W :	226.32
SMILES Code :	CC(C)(C)OC(=O)N1CCC2CNCCC12
MDL No. :	MFCD11877862
Boiling Point :	No data available
InChI Key :	HMLJDLIVSQQLPO-UHFFFAOYSA-N
Pubchem ID :	49761056

Safety of [ 1147422-00-1 ]

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

Computational Chemistry of [ 1147422-00-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	16
Num. arom. heavy atoms	0
Fraction Csp3	0.92
Num. rotatable bonds	3
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	70.81
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	41.57 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.85
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	1.27
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.84
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.	1.44
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	0.92
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.46

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.85
Solubility	3.23 mg/ml ; 0.0143 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.	-1.74
Solubility	4.1 mg/ml ; 0.0181 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	-1.65
Solubility	5.03 mg/ml ; 0.0222 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.	-6.78 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)	3.07

Application In Synthesis of [ 1147422-00-1 ]

* 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 [ 1147422-00-1 ]

[ 1147422-00-1 ] Synthesis Path-Downstream 1~18

1
[ 1147421-99-5 ]
[ 1147422-00-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	With hydrogen;5% palladium hydroxide on activated carbon; In methanol; ethanol; at 20.0℃; for 10.0h;	To a solution of (5-benzyl-octahydro-pyrrolo[3,2-c]pyridine-l-carboxylic acid tert- butyl ester (777 mg, 2.46 mmol) in IMS (20 mL) was added palladium hydroxide on carbon(5 %, 50 mg) and the mixture stirred under a hydrogen atmosphere at RT for 1O h. The reaction mixture was filtered through Celite and the filtrate concentrated in vacuo to give the title compound as a straw coloured oil (550 mg, 99 %).[M + H]+ 227.3

References: [1]Patent: WO2009/53715,2009,A1 .Location in patent: Page/Page column 75.

2
[ 1147422-00-1 ]
[ 501-53-1 ]
[ 1312784-22-7 ]

Yield	Reaction Conditions	Operation in experiment
63%	With triethylamine; In dichloromethane; at 20.0℃; for 4.0h;	1-Methyloctahydro-1H-pyrrolo[3,2-c]pyridine To a solution of <strong>[1147422-00-1]tert-butyl octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate</strong> (1.05 g, 4.64 mmol, Shah, S. K et. al, Bioorg. Med. Chem. Lett. 2005, 15, 977-982) in DCM (20 mL) was added TEA (1.29 mL, 9.29 mmol) followed by dropwise addition of benzyl chloroformate (0.795 mL, 5.57 mmol) at ambient temperature. After about 4 h, the mixture was diluted with DCM and then washed with water and brine. The organics were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with a gradient of 0-75% EtOAc in heptane to give 5-benzyl 1-tert-butyl hexahydro-1H-pyrrolo[3,2-c]pyridine-1,5(6H)-dicarboxylate (1.05 g, 63% yield): LC/MS (Table 1, Method a) Rt=2.59 min; MS m/z: 361 (M+H)+.

References: [1]Patent: US2011/152243,2011,A1 .Location in patent: Page/Page column 41.

3
[ 1147422-00-1 ]
[ 138021-99-5 ]

References: [1]Patent: US2011/152243,2011,A1 .

4
[ 1147422-00-1 ]
[ 1312784-23-8 ]

References: [1]Patent: US2011/152243,2011,A1 .

5
[ 1147422-00-1 ]
[ 1312784-24-9 ]

References: [1]Patent: US2011/152243,2011,A1 .

6
[ 24424-99-5 ]
[ 1147422-00-1 ]

References: [1]Patent: WO2013/71697,2013,A1 .
[2]Patent: US2014/228361,2014,A1 .

7
[ 148760-75-2 ]
[ 1147422-00-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With 10 wt% Pd(OH)2 on carbon; hydrogen; acetic acid; In 2-methoxy-ethanol; at 70.0℃; under 15001.5 Torr; for 24.0h;	To a solution of tert-butyl l H-pyrrolo[3,2-c]pyridine-l-carboxylate (2.55 g) in the mixture solvent of glycol monomethyl ether (40 mL) and AcOH (1 mL) was added a catalytic amount of Pd(OH)2/C. The suspension was heated at 70 C for 24 h under H2 (2.0 MPa) and filtered. The filtrate was concentrated in vacuo andthe residue was chromatographed with a silica gel column (eluting agent: 10: 1 (v/v) CH2Cl2/MeOH) to give the product as viscous liquid (2.64 g, 100.00 %).
100%	With 10 wt% Pd(OH)2 on carbon; hydrogen; In acetic acid; at 70.0℃; under 15001.5 Torr; for 24.0h;	To a solution of tert-butyl 1H-pyrrolo[3,2-c]pyridine-1-carboxylate (2.55 g) in the mixture solvent of glycol monomethyl ether (40 mL) and AcOH (1 mL) was added a catalytic amount of Pd(OH)2/C. The suspension was heated at 70 C. for 24 h under H2 (2.0 MPa) and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 10:1 (v/v) CH2Cl2/MeOH) to give the product as viscous liquid (2.64 g, 100.00%).

References: [1]Patent: WO2013/71697,2013,A1 .Location in patent: Paragraph 00276.
[2]Patent: US2014/228361,2014,A1 .Location in patent: Paragraph 0418-0419.

8
[ 271-34-1 ]
[ 1147422-00-1 ]

References: [1]Patent: WO2013/71697,2013,A1 .
[2]Patent: US2014/228361,2014,A1 .

9
[ 1147422-00-1 ]
[ 1438081-22-1 ]

References: [1]Patent: WO2013/71697,2013,A1 .
[2]Patent: US2014/228361,2014,A1 .

10
[ 1147422-00-1 ]
[ 1438072-89-9 ]

References: [1]Patent: WO2013/71697,2013,A1 .
[2]Patent: US2014/228361,2014,A1 .

11
[ 1147422-00-1 ]
[ 109-70-6 ]
[ 1438081-16-3 ]

Yield	Reaction Conditions	Operation in experiment
77%	With potassium carbonate; In acetone;Reflux;	To a solution of ieri-butyl octahydro-lH-pyrrolo[3,2-c]pyridine-l- carboxylate (0.63 g) in acetone (15 mL) was added 2C03 (1.54 g) and l -bromo-3-chloropropane (1.45 mL). The reaction mixture was heated to reflux overnight, diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous Na2S04 for 1 h and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 10: 1 (v/v) CH2Cl2/MeOH) to give the title compound as pale yellow liquid (0.65 g, 77.00 %).
77%	With potassium carbonate; In [(2)H6]acetone;Reflux;	To a solution of <strong>[1147422-00-1]tert-butyl octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate</strong> (0.63 g) in acetone (15 mL) was added K2CO3 (1.54 g) and 1-bromo-3-chloropropane (1.45 mL). The reaction mixture was heated to reflux overnight, diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4 for 1 h and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 10:1 (v/v) CH2Cl2/MeOH) to give the title compound as pale yellow liquid (0.65 g, 77.00%).

References: [1]Patent: WO2013/71697,2013,A1 .Location in patent: Paragraph 00277.
[2]Patent: US2014/228361,2014,A1 .Location in patent: Paragraph 0420-0421.

12
[ 1147422-00-1 ]
[ 69321-60-4 ]
tert-butyl 5-(3-bromo-2-methylphenyl)octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate [ No CAS ]