[ CAS No. 89088-69-7 ] {[proInfo.proName]}

Name: 89088-69-7|1-Methyl-1H-imidazol-4-amine hydrochloride|95%
Brand: Ambeed
SKU: A142498
Rating: 99 (28 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 89088-69-7 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 89088-69-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 89088-69-7 ]

SDS Specification

Alternatived Products of [ 89088-69-7 ]

Product Details of [ 89088-69-7 ]

CAS No. :	89088-69-7	MDL No. :	MFCD21340310
Formula :	C₄H₈ClN₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	STHPSKXDPYIGLM-UHFFFAOYSA-N
M.W :	133.58	Pubchem ID :	56956233
Synonyms :

Calculated chemistry of [ 89088-69-7 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.25
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	34.86
TPSA :	43.84 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.22 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	-0.15
Log Po/w (WLOGP) :	0.81
Log Po/w (MLOGP) :	-0.27
Log Po/w (SILICOS-IT) :	-0.26
Consensus Log Po/w :	0.03

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.04
Solubility :	12.3 mg/ml ; 0.092 mol/l
Class :	Very soluble
Log S (Ali) :	-0.32
Solubility :	64.5 mg/ml ; 0.483 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.35
Solubility :	59.1 mg/ml ; 0.443 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.37

Safety of [ 89088-69-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 89088-69-7 ]

* 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 [ 89088-69-7 ]
Downstream synthetic route of [ 89088-69-7 ]

[ 89088-69-7 ] Synthesis Path-Upstream 1~2

1
[ 79578-98-6 ]
[ 89088-69-7 ]

Reference： [1] Patent: WO2010/38060, 2010, A1, . Location in patent: Page/Page column 84

2
[ 3034-41-1 ]
[ 89088-69-7 ]

Reference： [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 1, p. 144 - 158
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 1, p. 265 - 285

[ 89088-69-7 ] Synthesis Path-Downstream 1~23

1
[ 89088-69-7 ]
[ 89088-68-6 ]

Reference： [1]Journal of Organic Chemistry,1984,vol. 49,p. 1224 - 1227

2
[ 126728-20-9 ]
[ 89088-69-7 ]
[ 1220517-86-1 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In ethanol; at 70℃;	Intermediate 23; 2-Chloro-Lambda/-(l-methyl-lH-imidazol-4-yl)pyridor2,3-dlpyrimidin-4-amine1 -Methyl- lH-imidazol-4-amine hydrochloride (Intermediate 36, 167 mg, 1.72 mmol), 2,4- dichloropyrido[2,3-d]pyrimidine (500 mg, 2.50 mmol) were suspended in ethanol (10 mL) and TEA (0.24mL, 1.72 mmol) was added. The reaction mixture was heated at 700C overnight and the title product was obtained after filtration (421mg).1H NMR (300 MHz, DMSO-d6) delta ppm 11.33 (s, 1 H) 9.16 (d, 1 H) 9.01 (s, 1 H) 7.54-7.72(m, 3H) 3.75 (s, 3 H). 103496-1PLCMS: 261 [M+H]4

Reference： [1]Patent: WO2010/38060,2010,A1 .Location in patent: Page/Page column 76-77
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 144 - 158

3
[ 79578-98-6 ]
[ 89088-69-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In ethanol; at 18 - 25℃; for 0.5h;	Intermediate 36; 1 -Methyl- lH-imidazol-4-amine hydrochlorideMel-Methyl-4-nitro-lH-imidazole (25 g, Intermediate 1) was dissolved in EtOH (800 ml) and Pd(OH)2 (2.5 g) was added. The mixture was subjected to an atmosphere of hydrogen for 3 hours at room temperature. The mixture was filtered and the organic layer was concentrated to give the 1 -methyl- lH-imidazol-4-amine. The amine was dissolved in EtOH (800ml) and stirred at room temperature. A saturated solution of EtOH with HCl gas (750ml) was added. The mixture was stirred for 30 minutes and the EtOH was concentrated under reduced pressure to 100ml, filtered, and washed with ether to give the title product (28.4 g). LCMS: 98 [M+Eta]+.

Reference： [1]Patent: WO2010/38060,2010,A1 .Location in patent: Page/Page column 84

4
[ 934524-10-4 ]
[ 89088-69-7 ]
[ 1220517-76-9 ]

Yield	Reaction Conditions	Operation in experiment
76%	With N-ethyl-N,N-diisopropylamine; In ethanol; at 88℃;	A solution of 1 -methyl- lH-imidazol-4-amine hydrochloride (Intermediate 36 , 16.39 g, 122.74 mmol) and 2,4-dichloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-J]pyrimidine (Intermediate 9, 21 g, 61.37 mmol) and DIPEA (42.9 ml, 245.47 mmol) in ethanol (264 ml) were heated at 88 0C overnight. The reaction mixture was cooled to 0 0C and filtered to provide 2-chloro-N-(l -methyl- lEta-imidazol-4-yl)-7-tosyl-7Eta-pyrrolo[2,3-d]pyrimidin-4-amine contaminated with DIPEA. The solid was dissolved in EtOAc (400 ml) and the solution was washed with water (3x100 ml). During the process, the title product crashed out of solution and collected through filtration. Concentration of the mother liquor provided additional title product (total=18.8 g, 76%). LCMS: 403 [M+H]+.1H NMR (300 MHz, DMSO-J6) deltappm 10.75 (br. s., 1 H), 7.96 (d, 2 H), 7.63 (d, 1 H),7.40 - 7.55 (m, 3 H), 7.35 (s, 1 H), 7.23 (br. s., 1 H), 3.68 (s, 3 H), 2.37 (s, 3 H)

Reference： [1]Patent: WO2010/38060,2010,A1 .Location in patent: Page/Page column 70
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 144 - 158

5
[ 98141-42-5 ]
[ 89088-69-7 ]
[ 1220517-85-0 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In ethanol; at 70℃;	Intermediate 22; 6-Chloro- 1 -methyl-iV-( 1 -methyl- lH-imidazol-4-yl)- lH-pyrazolo[3 ,4-<i1pyrimidin-4-amine4,6-Dichloro-l-methyl-lH-pyrazolo[3,4-d]pyrimidine (4.492 g, 22.12 mmol) and 1-methyl-lH- imidazol-4-amine hydrochloride (Intermediate 36, 2.96 g, 22.12 mmol) were suspended in ethanol (104 ml) and TEA (6.17 ml, 44.25 mmol) was added. The reaction mixture was then heated at 700C overnight. The reaction mixture was cooled to 00C and filtered providing the title product as a purple/grey solid (2.940 g). LCMS: 264[M+Eta]+.

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 144 - 158
[2]Patent: WO2010/38060,2010,A1 .Location in patent: Page/Page column 76

6
[ 1037479-62-1 ]
[ 89088-69-7 ]
[ 1220518-17-1 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In ethanol; at 60℃; for 2h;	Intermediate 69; 6-Chloro-iV-( 1 -methyl- lH-imidazol-4-vO- 1 -(tetrahvdro-2H-pyran-2-vO- 1 H-pyrazolo [3 A- dlpyrimidin-4-amineTo a solution of 4,6-dichloro-l-(tetrahydro-2H-pyran-2-yl)-lH-pyrazolo[3,4-d]pyrimidine(Intermediate 70, 3.168 g, 11.60 mmol) in ethanol (60 mL), was added TEA (4.04 mL, 29.00 mmol) followed by 1 -methyl- lH-imidazol-4-amine hydrochloride (Intermediate 36, 1.549 g,11.60 mmol). The resulting mixture was heated at 600C for 2 hours. Evaporation of the volatiles under reduced pressure gave a residue, which was purified utilizing ISCO (EtOAc/hexanes0->80%) to give the title product (1.56g).LCMS: 334 [M+Eta]+.

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 144 - 158
[2]Patent: WO2010/38060,2010,A1 .Location in patent: Page/Page column 101

7
[ 1220517-99-6 ]
[ 89088-69-7 ]
[ 1220517-98-5 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In ethanol; at 90℃; for 48h;	Intermediate 432-Chloro-7-(2-fluoroethyl)-Lambda/-(l -methyl- lH-imidazol-4-yl)-7H-pyrrolo[2,3-dlpyrimidin-4-amineThe solution of 2,4-dichloro-7-(2-fluoroethyl)-7H-pyrrolo[2,3-d]pyrimidine (Intermediate 44, 600 mg, 2.56 mmol) and 1 -methyl- lH-imidazol-4-amine hydrochloride (Intermediate 36, 523 mg, 3.08 mmol) was added to DIPEA (2686 mul, 15.38 mmol) in ethanol (5859 mul) and the reaction mixture was heated at 90 0C for 24 hours. Additional 1 -methyl- lH-imidazol-4-amine hydrochloride (Intermediate 36, 523 mg, 3.08 mmol) and DIPEA (2686 mul, 15.38 mmol) added to the reaction mixture and the mixture was heated at 90 0C for another 24 hours. The volatiles were removed under reduced pressure to afford a residue, which was dissolved in DCM/MeOH (10%) and washed with water. The organic layer was concentrated in vacuum, followed by purification by reversed phase HPLC (Gilson chromatography, 0%->50% MeCN/0.1% TFA H2O) to yield the title product (454 mg). LCMS: 297 [M+H]+.

Reference： [1]Patent: WO2010/38060,2010,A1 .Location in patent: Page/Page column 89

8
[ 1220517-82-7 ]
[ 89088-69-7 ]
[ 1220517-83-8 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In ethanol; at 0 - 25℃;	Intermediate 19; 1 -Ethyl-iV-d -methyl- lH-imidazol-4-yl)-6-(methylsulfonyl)- lH-pyrazolo[3 ,4-<i1pyrimidin-4- amine1 -Methyl- lH-imidazol-4-amine hydrochloride (Intermediate 36, 245 mg, 1.83 mmol) was dissolved in ethanol (5.090 mL) at 00C and TEA (1.022 mL, 7.33 mmol) and 4-chloro-l-ethyl-6- (methylsulfonyl)-lEta-pyrazolo[3,4-d]pyrimidine (Intermediate 18, 478 mg, 1.83 mmol) were added. The reaction was slowly allowed to warm to rt overnight. The reaction mixture was filtered providing the title product as an off-white solid (395 mg). 103496-1PLCMS: 322 [M+H]4

Reference： [1]Patent: WO2010/38060,2010,A1 .Location in patent: Page/Page column 74-75

9
[ 607-68-1 ]
[ 89088-69-7 ]
[ 1220518-16-0 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 144 - 158
[2]Patent: WO2018/232094,2018,A1 .Location in patent: Page/Page column 103; 104

10
[ 89088-69-7 ]
[ 90213-67-5 ]
[ 76-05-1 ]
[ 1220518-01-3 ]