186203-81-6|tert-Butyl hexahydro-1H-pyrrolo[3,4-b]pyridine-6(2H)-carboxylate| Ambeed

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Quality Control of [ 186203-81-6 ] Purity: 95% SDS Specification

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Product Details of [ 186203-81-6 ]

CAS No. :	186203-81-6
Formula :	C₁₂H₂₂N₂O₂
M.W :	226.32
SMILES Code :	O=C(N(C1)CC2C1CCCN2)OC(C)(C)C
MDL No. :	MFCD11858524
InChI Key :	LPNOEYLQBVUWGH-UHFFFAOYSA-N
Pubchem ID :	68729079

Safety of [ 186203-81-6 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302+H312-H315-H318-H411
Precautionary Statements:	P264-P270-P273-P280-P301+P312+P330-P302+P352+P312-P305+P351+P338+P310-P332+P313-P391-P501
Class:	9
UN#:	3077
Packing Group:	Ⅲ

Computational Chemistry of [ 186203-81-6 ] 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.	2.88
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	1.47

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)	3.14

Application In Synthesis of [ 186203-81-6 ]

* 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 [ 186203-81-6 ]

[ 186203-81-6 ] Synthesis Path-Downstream 1~9

Yield	Reaction Conditions	Operation in experiment
		Step 22k. cis-2,8-diaza-8-BOC-bicyclo[4.3.0]nonane The compound from step 22g is treated with H2 over Pd/C in ethanol, and the title compound is obtained by extraction from the reaction mixture.
		Step 23k. trans-2,8-diaza-8-BOC-bicyclo[4.3.0]nonane The compound from step 23g is treated with H2 over Pd/C in ethanol, and the title compound is obtained by extraction from the reaction mixture.

2
[ 24424-99-5 ]
[ 186203-81-6 ]

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

3
[ 1059172-92-7 ]
[ 186203-81-6 ]

Yield	Reaction Conditions	Operation in experiment
65%	With palladium 10% on activated carbon; hydrogen; In 2-methoxy-ethanol; at 70℃; for 6.0h;	To a solution of tert-butyl 5H-pyrrolo[3,4-b]pyridine-6(7H)-carboxylate (1.50 g) in glycol monomethyl ether was added a catalytic amount of 10% Pd/C. The suspension was heated to 70 C. and stirred for 6 h under H2. The resulted mixture was cooled to rt, poured into 100 mL of water and extracted with CH2Cl2 (50 mL×3). The combined organic phases were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo to give the title compound as pale yellow oil (0.95 g, 65.00%). The crude product was used for the next step without further purification. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 227.2 (M+1).
	With palladium 10% on activated carbon; hydrogen; In 2-methoxy-ethanol; at 70℃; for 6.0h;	To a solution of ier/-butyl 5H-pyrrolo[3,4-b]pyridine-6(7H)- carboxylate (1.50 g) in glycol monomethyl ether was added a catalytic amount of 10 % Pd/C. The suspension was heated to 70 C and stirred for 6 h under H2. The resulted mixture wascooled to rt, poured into 100 mL of water and extracted with CH2C12 (50 mL><3). The combined organic phases were dried over anhydrous Na2S04 and filtered. The filtrate was concentrated in vacuo to give the title compound as pale yellow oil (0.95 g, 65.00 %). The crude product was used for the next step without further purification.The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 227.2 (M+l).

References: [1]Patent: US2014/228361,2014,A1 .Location in patent: Paragraph 0494-0495.
[2]Patent: WO2013/71697,2013,A1 .Location in patent: Paragraph 00318.

4
[ 147739-88-6 ]
[ 186203-81-6 ]

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

5
[ 186203-81-6 ]
[ 1438082-78-0 ]

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

6
[ 186203-81-6 ]
[ 1438073-32-5 ]

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

7
[ 186203-81-6 ]
[ 1438073-38-1 ]

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

8
[ 186203-81-6 ]
[ 109-70-6 ]
[ 1438082-72-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetone; for 9.0h;Reflux;	A mixture of tert-but l hexahydro- l H-pyrrolo[3,4-b]pyridine-6(2H)- carboxylate (1.60 g), l -bromo-3-chloropropane (1.50 mL) and 2C03 (3.00 g) in acetone was heated to reflux for 9 h. The reaction mixture was cooled to rt and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 1 : 1 (v/v) PE/EA) to give the title compound as yellow oil (0.53 g, 65.00 %), HPLC: 89.00 %. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 303.2 (M+l ).
0.53 g	With potassium carbonate; In [(2)H6]acetone; for 9.0h;Reflux;	A mixture of <strong>[186203-81-6]tert-butyl hexahydro-1H-pyrrolo[3,4-b]pyridine-6(2H)-carboxylate</strong> (1.60 g), 1-bromo-3-chloropropane (1.50 mL) and K2CO3 (3.00 g) in acetone was heated to reflux for 9 h. The reaction mixture was cooled to rt and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 1:1 (v/v) PE/EA) to give the title compound as yellow oil (0.53 g, 65.00%), HPLC: 89.00%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 303.2 (M+1).

References: [1]Patent: WO2013/71697,2013,A1 .Location in patent: Paragraph 00319.
[2]Patent: US2014/228361,2014,A1 .Location in patent: Paragraph 0496-0497.

9
[ 186203-81-6 ]
[ 133311-51-0 ]
tert-butyl 1-(5-phenylthiazol-2-yl)octahydro-6H-pyrrolo[3,4-b]pyridine-6-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.163 g	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; CyJohnPhos; In toluene; at 20 - 110℃; for 16.0h;Inert atmosphere;	Step a. To a solution of 2-bromo-5-phenylthiazole (CAS Number 133311-51-0; 0.158 g, 0.660 mmol) in toluene (5 ml) was added <strong>[186203-81-6]tert-butyl octahydro-6H-pyrrolo[3,4-b]pyridine-6-carboxylate</strong> (CAS Number 186203-81-6; 0.150 g, 0.660 mmol) at rt. Sodium tert-butoxide (0.120 g, 1.30 mmol) was added to the reaction mixture at rt. The resulting reaction mixture was degassed for 15 min and then treated with Pd2(dba)3 (0.030 g, 0.033 mmol) and Cy-JohnPhos (0.011 g, 0.033 mmol). The resulting reaction mixture was heated at 110C for 16 h then cooled to rt and poured into water (50 ml). The obtained mixture was extracted with EtOAc (3 x 20 ml). The combined organic phase was dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (2% MeOH in DCM) yielding tert-butyl l-(5-phenylthiazol-2-yl)octahydro-6H- pyrrolo[3,4-b]pyridine-6-carboxylate (0.163 g, 0.422 mmol). LCMS: Method C, 2.766 min, MS: ES+ 386.38.

References: [1]Patent: WO2018/60742,2018,A1 .Location in patent: Page/Page column 59.

Historical Records

Technical Information

• Acyl Group Substitution • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • Hydride Reductions • Lawesson's Reagent • Preparation of Amines • Reactions of Amines • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes

Related Functional Groups of
[ 186203-81-6 ]

Amides

A455695 [159991-07-8]

(4aS,7aS)-tert-Butyl octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate

Similarity: 1.00

A123592 [1523571-18-7]

tert-Butyl 3,6-diazabicyclo[3.2.1]octane-6-carboxylate hydrochloride

Similarity: 0.98

A321330 [132414-81-4]

5-Boc-hexahydropyrrolo[3,4-b]pyrrole

Similarity: 0.98

A401583 [1214743-62-0]

tert-Butyl 3,6-diazabicyclo[3.2.2]nonane-6-carboxylate

Similarity: 0.98

A105660 [1277168-52-1]

(3aR,7aR)-rel-tert-Butyl hexahydro-1H-pyrrolo[3,2-b]pyridine-4(2H)-carboxylate

Similarity: 0.96

Related Parent Nucleus of
[ 186203-81-6 ]

Other Aliphatic Heterocycles

A455695 [159991-07-8]

(4aS,7aS)-tert-Butyl octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate

Similarity: 1.00

A123592 [1523571-18-7]

tert-Butyl 3,6-diazabicyclo[3.2.1]octane-6-carboxylate hydrochloride

Similarity: 0.98

A321330 [132414-81-4]

5-Boc-hexahydropyrrolo[3,4-b]pyrrole

Similarity: 0.98

A401583 [1214743-62-0]

tert-Butyl 3,6-diazabicyclo[3.2.2]nonane-6-carboxylate

Similarity: 0.98

A105660 [1277168-52-1]

(3aR,7aR)-rel-tert-Butyl hexahydro-1H-pyrrolo[3,2-b]pyridine-4(2H)-carboxylate

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H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 186203-81-6

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