[ CAS No. 127285-08-9 ] {[proInfo.proName]}

Name: 127285-08-9|4-Amino-1-isopropylpiperidine|97%
Brand: Ambeed
SKU: A457549
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Quality Control of [ 127285-08-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 127285-08-9 ]

CAS No. :	127285-08-9	MDL No. :	MFCD03411606
Formula :	C₈H₁₈N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZRQQXFMGYSOKDF-UHFFFAOYSA-N
M.W :	142.24	Pubchem ID :	3163333
Synonyms :

Calculated chemistry of [ 127285-08-9 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	47.97
TPSA :	29.26 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.68 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.05
Log Po/w (XLOGP3) :	0.68
Log Po/w (WLOGP) :	0.44
Log Po/w (MLOGP) :	0.9
Log Po/w (SILICOS-IT) :	0.68
Consensus Log Po/w :	0.95

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.08
Solubility :	11.7 mg/ml ; 0.0824 mol/l
Class :	Very soluble
Log S (Ali) :	-0.87
Solubility :	19.1 mg/ml ; 0.134 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.81
Solubility :	21.9 mg/ml ; 0.154 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.19

Safety of [ 127285-08-9 ]

Signal Word:	Danger	Class:	8,3
Precautionary Statements:	P210-P280-P370+P378-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310	UN#:	2920
Hazard Statements:	H314-H226	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 127285-08-9 ]

* 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.

Upstream synthesis route of [ 127285-08-9 ]
Downstream synthetic route of [ 127285-08-9 ]

[ 127285-08-9 ] Synthesis Path-Upstream 1~6

1
[ 609804-23-1 ]
[ 127285-08-9 ]

Yield	Reaction Conditions	Operation in experiment
98%	at 20℃; for 20 h;	General procedure: To a solution of compound I-5 (240 mg) in HFIP (8 mL), 10percent Pd/C (120 mg) was added and thenthe reaction mixture was stirred under H2 at room temperature and 1atm for 20 h. Then themixture was filtrated and the filtrate was concentrated to give compound I-6 as yellow oil (100 mg,75percent).

Reference： [1] European Journal of Medicinal Chemistry, 2017, vol. 132, p. 26 - 41
[2] Patent: EP1489078, 2004, A1, . Location in patent: Page 130

2
[ 534595-37-4 ]
[ 127285-08-9 ]

Yield	Reaction Conditions	Operation in experiment
79.3%	Stage #1: With trifluoroacetic acid In methanol at 0℃; for 18 h; Stage #2: With potassium hydroxide In water	The compound (14a) (1.5 g, 7.49 mmol) obtained in PreparationExample (1-iii-l) was dissolved in methanol (20 ml) in a 250 ml vessel, and trifluoroacetic acid (4.06 ml, 54.5 mmol, 5 eq.) was added dropwise thereto while stirring. The resulting mixture was reacted for 18 hrs. After the completion of reaction, the mixture was concentrated under reduced pressure, and then subjected to azeotropic distillation with CHCl₃ 3 times. The reaction mixture was basified with aqueous KOH solution (20 ml) and extracted with CHCl₃ 3 times. The organic layer was separated, washed with brine, dried, filtered and distilled under reduced pressure, to obtain 1.23 g of the title compound as yellow oil (yield 79.3percent).¹H-NMR (200 MHz, CDCl₃) δ 1.02 (d, J = 6.6 Hz, 6H), 1.38 (m, 2H), 1.56 (br, 2H), 1.80 (d, J = 11.8 Hz, 2H), 2.17 (m, 2H), 2.71 (m, 2H), 2.80 (m, 2H).LC/MS (M⁺H): 143; ^-Butyl-l-isopropylpiperidin-4-ylcarbamate (2.64 g, 10.9 mmol) obtained in Preparation Example (2-iii-l) was dissolved in methanol (20 ml) in a 250 ml vessel at 0^°C, and trifluoroacetic acid (TFA; 4.06 ml, 54.5 mmol, 5 eq.) was slowly added thereto while stirring. The resulting mixture was reacted for 18 hrs. After the completion of reaction, the reaction product was concentrated under reduced pressure, subjected to azeotropic distillation with CHCl₃ 3 times, basified with 2N aqueous KOH solution (20 ml) and extracted with CHCl₃ 3 times. The organic layer was separated, washed with brine, dried, filtered and distilled under reduced pressure to obtain 1.23 g of the title compound as yellow oil (yield 79.3percent).¹H-NMR (200 MHz, CDCl₃) δ 1.02 (d, J = 6.6 Hz, 6H), 1.38 (m, 2H), EPO <DP n="81"/>1.56 (br, 2H), 1.80 (d, J = 11.8 Hz, 2H), 2.17 (m, 2H), 2.71 (m, 2H), 2.80 (m, 2H).LC/MS (M⁺H): 143; The compound (14 a) (2.64 g, 10.9 mmol) obtained in PreparationExample (4-iii-l) was dissolved in methanol (20 ml) in a 250 ml vessel, and 0 trifluoroacetic acid (4.06 ml, 54.5 mmol, 5 eq.) was added dropwise thereto while stirring. The resulting mixture was reacted for 18 hrs. After the completion of reaction, the mixture was concentrated under reduced pressure, and then subjected to azeotropic distillation with CHCl₃ 3 times. The reaction mixture was basified with aqueous KOH solution (20 ml) and 5 extracted with CHCl₃ 3 times. The organic layer was separated, washed with brine, dried, filtered and distilled under reduced pressure, to obtain 1.229 g of the title compound as yellow oil (yield 79.3percent).¹H-NMR (200 MHz, CDCl₃) δ 1.02 (d, J = 6.6 Hz, 6H), 1.38 (m, 2H), 1.56 (br, 2H), 1.80 (d, J = 11.8 Hz, 2H), 2.17 (m, 2H), 2.71 (m, 2H), 2.80 (m, 0 2H).LC/MS (M⁺H): 143.
79.3%	Stage #1: With trifluoroacetic acid In methanol for 18 h; Stage #2: With potassium hydroxide In water	The compound (14a) obtained in Preparation Example (III- 1 ) (1.5 g, 7.49 mmol) was dissolved in methanol (20 ml) in the 250 ml reaction vessel, trifluoro acetic acid (4.06 ml, 54.5 mmol, 5 eq.) was added dropwise thereto <n="22"/>while stirring, and kept for 18 hrs. After the completion of the reaction, the mixture was concentrated under a reduced pressure, and then subjected to azeotropic distillation with CHCl₃ 3 times. The reaction mixture was basified with aqueous KOH solution (20 ml) and extracted with CHCl₃ 3 times. The extract was washed with salt water, dried, filtered and distilled under a reduced pressure, to obtain 1.23 g of the title compound as yellow oil (yield: 79.3percent).¹H-NMR (200 MHz, CDCl₃) δ 1.02 (d, J = 6.6 Hz, 6H), 1.38 (m, 2H), 1.56 (br, 2H), 1.80 (d, J = 11.8 Hz, 2H), 2.17 (m, 2H), 2.71 (m, 2H), 2.80 (m, 2H). LC/MS (M+H): 143

Reference： [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 14, p. 4511 - 4525
[2] Patent: WO2008/54154, 2008, A1, . Location in patent: Page/Page column 36; 79-80; 166
[3] Patent: WO2007/52938, 2007, A1, . Location in patent: Page/Page column 20-21
[4] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 16, p. 4191 - 4195
[5] Patent: US2003/199689, 2003, A1, . Location in patent: Page/Page column 24
[6] Patent: WO2004/50636, 2004, A2, . Location in patent: Page 87
[7] Patent: EP1479677, 2004, A1, . Location in patent: Page 52
[8] Patent: US2005/33049, 2005, A1, . Location in patent: Page/Page column 39
[9] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 5, p. 1623 - 1642

3
[ 73874-95-0 ]
[ 127285-08-9 ]

Reference： [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 14, p. 4511 - 4525
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 16, p. 4191 - 4195
[3] Patent: EP1433788, 2004, A1, . Location in patent: Page 41

4
[ 220394-97-8 ]
[ 127285-08-9 ]

Reference： [1] European Journal of Medicinal Chemistry, 2017, vol. 132, p. 26 - 41

5
[ 87120-72-7 ]
[ 127285-08-9 ]

Reference： [1] European Journal of Medicinal Chemistry, 2017, vol. 132, p. 26 - 41

6
[ 182223-54-7 ]
[ 127285-08-9 ]

Reference： [1] European Journal of Medicinal Chemistry, 2017, vol. 132, p. 26 - 41

[ 127285-08-9 ] Synthesis Path-Downstream 1~87

1
[ 906462-83-7 ]
[ 127285-08-9 ]
5-(2-chloro-phenyl)-1-(2,6-dichloro-phenyl)-7-(1-isopropyl-piperidin-4-ylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 4400 - 4404

2
[ 904677-87-8 ]
[ 127285-08-9 ]
[(1-Isopropylpiperidin-4-ylamino)(4-piperidinopiperidino)methylene]malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	at 60℃; for 2h;	(Step 2) [(Methylthio)(4-piperidinopiperidino)methylene] malononitrile (613 mg, 2.11 mmol) obtained in the Step 1 and <strong>[127285-08-9]4-amino-1-isopropylpiperidine</strong> (1.20 g, 8.44 mmol) are mixed and stirred at 60C for 2 hours. After cooling, the mixture was added with diisopropylether (5 mL) and hexane (10 mL), followed by stirring at room temperature for 0.25 hour. After the mixture was let stand for a while, the supernatant was removed and the residue was purified by NH silica gel column chromatography (hexane/chloroform (1:9) to chloroform) to obtain the titled compound (499 mg, 61 %) as a yellow oily substance. 1H NMR (CDCl3,deltappm): 1.03 (d, J = 6.6 6 Hz, 6H), 1.44-1.75 (m, 10H), 1.93-2.02 (m, 4H), 2.27 (td, J = 2.3, 11.7 Hz, 2H), 2.48-2.51 (m, 5H), 2.75 (sept, J = 6.6 Hz, 1H), 2.84 (d, J = 11.7 Hz, 2H), 3.10 (td, J =2.1, 12.7Hz, 2H), 3.40-3.52 (m, 1H), 3.85 (d, J = 12.7 Hz, 2H), 4.39 (d, J =9.2 Hz, 1H). APCIMS m/z: [M+H]+385.

Reference： [1]Patent: EP1847530,2007,A1 .Location in patent: Page/Page column 143

3
[ 904677-50-5 ]
[ 127285-08-9 ]
[(1-Isopropylpiperidin-4-ylamino)(4-piperidinomethylpiperidino)methylene]malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	at 60℃; for 6h;	Example 178 [(1-Isopropylpiperidin-4-ylamino)(4-piperidinomethylpiperidino)methylene]malononitrile (Compound 178) [(Methylthio)(4-piperidinomethylpiperidino) methylene]malononitrile (535 mg, 1.76 mmol) obtained in Step 1 of Example 147 and <strong>[127285-08-9]4-amino-1-isopropylpiperidine</strong> (1.00 g, 7.03 mmol) were mixed and the mixture was stirred at 60C for 6 hours. After cooling, the reaction mixture was purified by NH silica gel column chromatography (chloroform) to obtain the titled compound (222 mg, 32 %) as a yellow oily substance. 1H NMR (CDCl3, deltappm): 1.04 (d, J = 6.5 Hz, 6H), 1.10-1.34 (m, 4H), 1.34-1.67 (m, 7H), 1.67-2.09 (m, 6H), 2.09-2.20 (m, 1H), 2.20-2.43 (m, 5H), 2.77 (sept, J = 6.5 Hz, 1H), 2.81-2.92 (m, 2H), 3.08 (t, J =12.8 Hz, 2H), 3.42-3.56 (m, 1H), 3.80 (d, J = 12.8 Hz, 2H), 4.45 (d, J = 8.9Hz,1H).

Reference： [1]Patent: EP1847530,2007,A1 .Location in patent: Page/Page column 144

4
[ 904677-53-8 ]
[ 127285-08-9 ]
{(1-isopropylpiperidin-4-ylamino)[4-(2-methylpyrrolidin-1-ylmethyl)piperidino]methylene}malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%	at 60℃; for 8h;	Example 180 {(1-Isopropylpiperidin-4-ylamino)[4-(2-methylpyrrolidin-1-ylmethyl)piperidino]methylenel malononitrile (Compound 180) [4-(2-Methylpyrrolidin-1-ylmethyl)piperidino] (methylthio)methylene}malononitrile (535 mg, 1.76 mmol) obtained in Step 1 of Example 148 and <strong>[127285-08-9]4-amino-1-isopropylpiperidine</strong> (1.00 g, 7.03 mmol) were mixed and the mixture was stirred at 60C for 8 hours. After cooling, the solvent was evaporated under reduced pressure and the residue was purified by NH silica gel column chromatography (chloroform). The obtained solid was washed with diisopropylether and the titled compound (194 mg, 28 %) was obtained as a white solid. 1H NMR (CDCl3, deltappm): 1.04 (d, J = 5.9 Hz, 3H), 1.05 (d,J=6.6 Hz, 6H), 1.16-1.45 (m, 3H), 1.52-1.94 (m, 7H), 1.97-2.12 (m, 5H), 2.23-2.36 (m, 3H), 2.55 (dd, J = 9.6, 12.1 Hz, 1H), 2.79 (sept, J = 6.6Hz, 1H), 2.83-2.92 (m, 2H), 3.01-3.18 (m, 3H), 3.44-3.58 (m, 1H), 3.74-3.88 (m, 2H), 4.46 (d, J =8. 9 Hz, 1H).

Reference： [1]Patent: EP1847530,2007,A1 .Location in patent: Page/Page column 144-145

5
[ 946822-60-2 ]
[ 127285-08-9 ]
4-(9-cyclopentyl-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-N-(1-isopropyl-piperidin-4-yl)-3-methoxy-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 18 - 25℃; for 3h;	4-[(2-cyclopentyl-6-methyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-3-methoxy-benzoic acid (Example 111; 100 mg, 0.24 mmol), N-Isopropyl-4-aminopiperidine (ABCR, 42 mg, 0.29 mmol), HATU (111 mg, 0.29 mmol) and DIPEA (127 uL, 0.73 mmol) and DMF (3 mL) were combined and stirred at room temperature for 3 hours. The solvent was evaporated and the residue partitioned between DCM (10 mL) and water (10 mL). The organic phase was added to a 5 g SCX-2 column pre-wet with MeOH (2 column volumes), flushed with MeOH (2 column volumes) and the crude product eluted with 2M ammonia in MeOH and solvents evaporated. The residue was taken up in DCM and purified on silica, eluting with a gradient of 0-5% MeOH/DCM followed by 5% then 10% and finally 15% MeOH/DCM. Fractions containing product were combined and evaporated to give the tile compound as a white solid (45 mg, 35%).1H NMR (400.132 MHz, CDCl3) delta0.99 (d, 6H), 1.55-1.73 (m, 8H), 2.00 (m, 4H), 2.27 (m, 2H), 2.60 (m, 2H), 2.69 (m, 1H), 2.81 (m, 2H), 3.22 (s, 3H), 3.62 (m, 2H), 3.92 (m, 4H), 4.83 (m, 1H), 5.82 (d, 1H), 7.14 (m, 1H), 7.35 (d, 1H), 7.59 (s, 1H), 7.87 (s, 1H), 8.43 (d, 1H); MS m/z 536 [M+H]+.

Reference： [1]Patent: US2008/9482,2008,A1 .Location in patent: Page/Page column 30

6
[ 73874-95-0 ]
[ 127285-08-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In methanol; water; for 16h;	(ii) 1-Isopropyl-piperidin-4-ylamine To 4.8 g (1-Isopropyl-piperidin-4-yl)-carbamic acid tert-butyl ester in 15 ml methanol, 20 ml methanolic hydrochloric acid (8M) were added and the mixture was stirred for 16 h. Removal of the solvent under reduced pressure yielded a white solid, which was coevaporated twice with 20 ml toluene. The product was obtained as its hydrochloride. Yield: 5.42 gMS (ES+): m/e= 143.

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 4511 - 4525
[2]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4191 - 4195
[3]Patent: EP1433788,2004,A1 .Location in patent: Page 41

7
[ 127285-08-9 ]
1-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-6-methyl-1H-indole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide [ No CAS ]