[ CAS No. 186692-46-6 ] {[proInfo.proName]}

Name: 186692-46-6|(R)-2-((6-(Benzylamino)-9-isopropyl-9H-purin-2-yl)amino)butan-1-ol|98%
Brand: Ambeed
SKU: A300507
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Quality Control of [ 186692-46-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 186692-46-6 ]

SDS Specification

Alternatived Products of [ 186692-46-6 ]

Product Details of [ 186692-46-6 ]

CAS No. :	186692-46-6	MDL No. :	MFCD02266401
Formula :	C₁₉H₂₆N₆O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BTIHMVBBUGXLCJ-OAHLLOKOSA-N
M.W :	354.45	Pubchem ID :	160355
Synonyms :	CYC202;Seliciclib;Roscovitin;R-roscovitine;Roscovitine

Calculated chemistry of [ 186692-46-6 ]

Physicochemical Properties

Num. heavy atoms :	26
Num. arom. heavy atoms :	15
Fraction Csp3 :	0.42
Num. rotatable bonds :	8
Num. H-bond acceptors :	4.0
Num. H-bond donors :	3.0
Molar Refractivity :	104.88
TPSA :	87.89 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.6
Log Po/w (XLOGP3) :	3.16
Log Po/w (WLOGP) :	2.67
Log Po/w (MLOGP) :	1.61
Log Po/w (SILICOS-IT) :	2.09
Consensus Log Po/w :	2.63

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.93
Solubility :	0.0419 mg/ml ; 0.000118 mol/l
Class :	Soluble
Log S (Ali) :	-4.68
Solubility :	0.00747 mg/ml ; 0.0000211 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.82
Solubility :	0.00054 mg/ml ; 0.00000152 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	3.58

Safety of [ 186692-46-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302+H312+H332-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 186692-46-6 ]

* 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 [ 186692-46-6 ]

[ 186692-46-6 ] Synthesis Path-Downstream 1~8

1
[ 5856-63-3 ]
[ 186692-41-1 ]
[ 186692-46-6 ]

Reference： [1]Organic Process Research and Development,2009,vol. 13,p. 641 - 644
[2]Journal of Medicinal Chemistry,1997,vol. 40,p. 408 - 412
[3]Tetrahedron Asymmetry,2001,vol. 12,p. 2891 - 2894
[4]Journal of Medicinal Chemistry,2008,vol. 51,p. 5229 - 5242

2
[ 39639-47-9 ]
[ 186692-46-6 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 408 - 412

3
[ 3800-23-5 ]
[ 186692-46-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6949 - 6965

4
[ 482615-52-1 ]
[ 5856-63-3 ]
[ 186692-46-6 ]

Yield	Reaction Conditions	Operation in experiment
93%	With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; butan-1-ol; at 140℃; for 48.0h;Inert atmosphere;	To a stirred solution of 6-benzylamino-2-fluoro-9-isopropylpurine (4d, 0.50 g, 1 equiv, 1.75 mmol) in n-BuOH/DMSO (10 mL, 4:1) at room temperature under an argon atmosphere was added DIEA (3.0 mL, 9.82 equiv, 17.22 mmol) followed by (R)-(-)-2-aminobutan-1-ol (R-5) (1.6 mL, 10 equiv, 17.0 mmol). The reaction mixture was placed in a preheated oil bath at 140 C and stirred at this temperature for 48 h, when TLC DCM/ether/MeOH (55:40:5) indicated that the reaction had gone to completion. The reaction mixture was allowed to cool to room temperature and the solvent was evaporated in vacuo. The residue was partitioned between DCM (100 mL) and water (150 mL), the aqueous phase was extracted with more DCM (2 × 50 mL), and the combined organic phase was washed with brine (50 mL), dried (MgSO4) and evaporated in vacuo. The residue was purified by gradient column chromatography on silica gel eluted with DCM/ether/MeOH (50:50:0?50:50:1) to afford 6-benzylamino-2-[(R)-1-ethyl-2-hydroxyethylamino]-9-isopropylpurine (alphaR-1) as a white solid; yield: 0.58 g (93%). Mp 104-105 C. 1H NMR (DMSO-d6, 250 MHz): delta 0.82 (t, 3H, J = 7.33 Hz, -NHCH(CH2CH3)CH2OH), 1.45 (m, 8H, -NHCH(CH2CH3)CH2OH + -CH)CH3)2), 3.30-3.42 (m, 2H, -NHCH(CH2CH3)CH2OH), 3.70 (m, 1H, -NHCH(CH2CH3)CH2OH), 4.51 (m, 4H, -HNCH2-Bz, OH + -CH(CH3)2), 5.80 (d, 2H, J = 8.37 Hz, -NHCH(CH2CH3)CH2OH), 7.17-7.35 (m, 5H, Bz), 7.76 (b s, 2H, -NCH-N- + -HNCH2-Bz). FABMS m/z (relative intensity): 355 ([M+H]+, 100), 323 (52), 154 (10), 134 (14). Accurate mass (M+H): actual: 355.2246, measured: 355.2260. Microanalysis (expected: measured) C19H26N6O: C; 64.38: 64.21, H; 7.39: 7.44, N; 23.71: 23.37.

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6949 - 6965

5
[ 1651-29-2 ]
[ 186692-46-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6949 - 6965

6
[ 100-46-9 ]
[ 186692-46-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6949 - 6965

7
[ 104963-54-4 ]
[ 186692-46-6 ]
[ 1428319-98-5 ]

Yield	Reaction Conditions	Operation in experiment
48%	With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In pyridine; at 20℃; for 4.0h;	Compound 1 (80 mg, 0.225 mmol) was solubilized in dry pyridine (10 mL). 4-Nitrooxybutirric acid26 (74 mg, 0.495 mmol), EDC (52 mg, 0.27 mmol) and DMAP (cat.) were added and the mixture was stirred at room temperature for 4 h. The mixture was treated with HCl 1 N, extracted with CH2Cl2 (3 × 15 mL) and the combined organic phases were washed with HCl 1 N (3 × 10 mL), brine (20 mL), dried (Na2SO4), filtered and evaporated in vacuo. The crude residue was purified by flash cromatography eluting with CH2Cl2 gradient to CH2Cl2/MeOH 1% to obtain the pure product as a yellow oil (50 mg, yield 48%). MS/CI (isobutane): [M+1]+ 486. 1H NMR (CDCl3): delta, 7.36 (s, 1H, H8), 7.33-7.21 (m, 5H, HAr), 6.47 (s br, 1H, NH(6)), 4.80-4.77 (m, 3H, CHNH(2) and CH2Ph), 4.65-4.55 (m, 1H, CH(CH3)2), 4.44 (t, 2H, CH2ONO2), 4.24-4.16 (m, 3H, CH2O(CO) and CHNH), 2.41 (t, 2H, CH2(CO)O), 2.04-1.97 (m, 2H, CH2CH2CH2), 1.68-1.49 (m, 8H, CH2CH3 and CH(CH3)2), 0.97 (t, 3H, CH2CH3). 13C NMR (CDCl3): delta, 172.3, 160.0, 154.9, 151.0, 139.4, 134.6, 128.5, 127.6, 127.1, 114.6, 72.0, 66.2, 51.5, 46.2, 44.3, 30.1, 24.9, 22.58, 22.57, 22.2, 10.6. HPLC purity (CH3CN/H2O + 0.1% TFA, 1/1): 99%. Elemental analysis for C23H31N7O5. Calculated: C, 56.90; H, 6.44; N, 20.19. Found: C, 57.49; H, 6.46; N, 19.99.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 2107 - 2116

8
C₂₉H₃₉N₃O₅ [ No CAS ]
[ 186692-46-6 ]
(R)-2-((6-(benzylamino)-9-isopropyl-9H-purin-2-yl)amino)butyl (2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenamido)ethyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 24.0h;Reflux;	Example 20 Preparation of (R)-2-((6-(benzylamino)-9-isopropyl-9H-purin-2-yl)amino)butyl (2- -icosa-5,8,ll,14,17-pentaenamido)ethyl)carbamate (IV-16): [0316] In a typical run, (5Z,8Z,1 lZ,14Z,17Z)-N-(2-aminoethyl)icosa-5,8,l 1,14,17- pentaenamide (69 mg, 0.2 mmol) was taken up in 5 mL anhydrous of CH2CI2 along with 4- nitrophenyl chloroformate (0.26 mmol). Triethylamine (56 mu, 0.4 mmol) was then added dropwise at room temperature. The resulting reaction mixture was stirred at rt for 16 h. (R)- 2-((6-(Benzylamino)-9-isopropyl-9H-purin-2-yl)amino)butan-l-ol (42 mg, 0.12 mmol) was then added in a single portion at rt to this freshly prepared mixture of 4-nitrophenyl carbamate derivative. Once DIEA (200 mu, 1.2 mmol) was added, the reaction mixture was stirred at a gentle reflux for 24 h. The crude reaction mixture was diluted with 25 mL of EtOAc. The resulting organic layer was washed with brine (3 x 5 mL), dried over Na2S04 and concentrated under reduced pressure. The crude material was purified over a silica gel chromatography (gradient elution: 0-10% MeOH in 0.2% triethylamine spiked dichloromethane). MS (EI) calculated for 724.98; Found: 725.6 [M+H] +

Reference： [1]Patent: WO2014/204856,2014,A1 .Location in patent: Paragraph 0315-0316

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[ CAS No. 186692-46-6 ] {[proInfo.proName]}

Quality Control of [ 186692-46-6 ]

Related Doc. of [ 186692-46-6 ]

Product Details of [ 186692-46-6 ]

Calculated chemistry of [ 186692-46-6 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 186692-46-6 ]

Application In Synthesis of [ 186692-46-6 ]

[ 186692-46-6 ] Synthesis Path-Downstream 1~8

Precautionary Statements-General

Prevention

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Health hazards

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