[ CAS No. 914942-88-4 ] {[proInfo.proName]}

Name: 914942-88-4|tert-Butyl (6-amino-7-iodo-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)(methyl)carbamate|95%
Brand: Ambeed
SKU: A509016
Rating: 98 (22 reviews)

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

2D 3D

Structure of 914942-88-4 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 914942-88-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 914942-88-4 ]

SDS Specification

Alternatived Products of [ 914942-88-4 ]

Product Details of [ 914942-88-4 ]

CAS No. :	914942-88-4	MDL No. :	MFCD29058807
Formula :	C₁₃H₁₈IN₅O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JZLKAZMOZMXQIY-UHFFFAOYSA-N
M.W :	403.22	Pubchem ID :	46894439
Synonyms :

Calculated chemistry of [ 914942-88-4 ]

Physicochemical Properties

Num. heavy atoms :	21
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.46
Num. rotatable bonds :	4
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	91.06
TPSA :	86.27 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.52 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.68
Log Po/w (XLOGP3) :	1.75
Log Po/w (WLOGP) :	2.53
Log Po/w (MLOGP) :	1.88
Log Po/w (SILICOS-IT) :	0.93
Consensus Log Po/w :	1.95

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.5
Solubility :	0.129 mg/ml ; 0.000319 mol/l
Class :	Soluble
Log S (Ali) :	-3.18
Solubility :	0.267 mg/ml ; 0.000662 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.23
Solubility :	0.235 mg/ml ; 0.000583 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.22

Safety of [ 914942-88-4 ]

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

Application In Synthesis of [ 914942-88-4 ]

* 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 [ 914942-88-4 ]

[ 914942-88-4 ] Synthesis Path-Downstream 1~78

1
[ 914942-88-4 ]
[ 3032-92-6 ]
[ 914944-37-9 ]

Yield	Reaction Conditions	Operation in experiment
60%	With triethylamine; In N,N-dimethyl-formamide; at 90℃; for 0.416667h;	Al.12 (1.0 g, 2.48 mmol), dichlorobis(triphenylphosrhohme)palladium (24 mg,0.12 mmol);, 4-ethynylbenzonitrile (631mg, 4.96 mmol) and triethylamine (0.7 mL,5.0mmol) were each added to N,N-dimethylformamide (10 mL) and nitrogen bubbled through the resulting mixture for 5min. The reaction mixture was heated at 90 0C for EPO <DP n="132"/>20 min under a nitrogen atmosphere before cooling to room temperature and evaporating the solvent in vacuo. The residue was purified by silica gel column chromatography using ethyl acetate as eluent to provide 0.58g (60%) of A105a.l. HPLC YMC S-5 4.6x33mm (2min grad): retention time 1.69min,M+H+ = 403.35.

Reference： [1]Patent: WO2006/122137,2006,A1 .Location in patent: Page/Page column 130-131

2
[ 914942-88-4 ]
[ 536-74-3 ]
[ 914942-89-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	With copper(l) iodide; diisopropylamine;bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 60℃; for 0.5h;Product distribution / selectivity;	A suspension of Al.12 (1.0 g, 248 tnmol) in DMF (6.80 mL) was degassed by bubbling argon through the solvent. Phenylacetylene was added (0.68 mL, 6.2 mmol), followed by dichlorobis(triphenyl-phosphine)palladium II (0.10 g, 0.149 mmol), copper (I) iodide (28.4 mg, 0.06 mmol), and degasssed diisopropylamine (9.2 mL). The pressure tube was sealed and immediately immersed in a 60 0C oil bath, and stirred for 30 min. The reaction mixture was evaporated to dryness under vacuum. The crude product was partitioned between EtOAc (45 mL) and water. After separation, the EtOAc layer was washed with water, brine, dried (NaOSO4), and concentrated under reduced pressure to yield over 1.0 g of a brown taffy. Flash chromatography on silica gel, eluting with a hexane : EtOAc gradient yielded 0.94 g, (98%) of Al.13 as a pale yellow powder. HPLC (condition C): 92.9%, ret. Time 2.91 min., LC/MS (M+H)+ - 378.4.
	With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; In dichloromethane; at 40℃; for 24h;Product distribution / selectivity;	Copper iodide (5.0mg, 0.025mmol) and dichlorobis(triphenylphosphine) palladium (4.0mg, 0.050mmol) were each added in one portion to a mixture of Al.12 (lOOmg, 0.25mmol), phenylacetylene (28mg, 0.28mmol) and triethylamine (0.11ml, 0.75mmol) in dichloromethane (0.5ml) at room temperature under a nitrogen atmosphere. The resulting mixture was heated to 40 0C for 24hrs before cooling to room temperature and evaporating in vacuo. The residue was purified by column chromatography using ethyl acetate as eluent to give 62mg of A1.13. LC/MS Phenomenex S5 4.6x30mm (2min gradient) Found: M+H = 378.27 at 1.51 min

Reference： [1]Patent: WO2006/122137,2006,A1 .Location in patent: Page/Page column 79
[2]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2646 - 2649
[3]Patent: WO2006/122137,2006,A1 .Location in patent: Page/Page column 79

3
[ 914942-88-4 ]
[ 127-17-3 ]
[ 914944-74-4 ]

Yield	Reaction Conditions	Operation in experiment
62%	With triethylamine;tris-(dibenzylideneacetone)dipalladium(0); In N,N-dimethyl-formamide; at 120℃; for 0.25h;Microwave irradiation;	Al.12 (0.3g, 0.74 mm ol), pyruvic acid (98mg, 1.12mmol), triethylamine and palladium dibenzylidene acetone (68mg, 0.074mmol) in dry DMF (3mL) were heated to 120C for 15 min in a microwave. The reaction mixture was diluted with water (3 mL) and extracted with ethyl acetate (10 niL). The organic extract was discarded and the aqueous layer acidified to pH 3-4 using IN HCL The acidified aqueous layer was then extracted with ethyl acetate (3 x 20 mL), the combined organics dried (MgSO4) and evaporated in vacuo to give A168.1 (lbetalmg, 62%). HPLC YMC S-5 4.6x33mm EPO <DP n="148"/>W(2min grad): retention time 1.32min, M+H+ = 346.31, NMR (400MHz, DMSO) delta 12.49 (s, IH), 8.16 (s, IH), 7.47 (s, IH), 4.04 (s, 3H), 3.29 (s, 3H), 1.30 (s, 9H).

Reference： [1]Patent: WO2006/122137,2006,A1 .Location in patent: Page/Page column 146

4
[ 914942-88-4 ]
[ 171290-53-2 ]
[ 914942-92-0 ]

Yield	Reaction Conditions	Operation in experiment
65 - 81%	With triethylamine;bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 90℃; for 0.416667 - 0.833333h;Product distribution / selectivity;	A1.12 (1.48 g, 3.66 mmol), dichlorobis(triphenylphosphine)palladium (155 mg, 0.22 mmol), 3-ethynylbenzonitrile (A2.2) (930 mg, 7.32 mmol) and triethylamine (12 mL) were added to N,N-dimethylformamide (8 mL). The reaction mixture was heated at 90 0C for 50 min, cooled and the solvent removed under reduced pressure. The residue was purified by silica gel column chromatography using ethyl acetate as the eluent to provide 960mg (65%) of A2.3. M+H+ = 403.21. Alternate preparation:A1.12 (8.0 g, 19.85 mmol), dichlorobis(trirhohenylphosphine)palladium (840 mg, 1.2 mmol), 3-ethynylbenzonitrile (A2.2) (3.2g, 25.0 mmol) and triethylamine (60 mL) were each added to N,N-dimethylformamide (40 mL), and nitrogen was bubbled through the resulting mixture for 5min. The reaction mixture was heated at 90 0C for 20 min under a nitrogen atmosphere before cooling to room temperature and evaporating the solvent in vacuo. The residue was purified by silica gel column chromatography using ethyl acetate as eluent to provide 6.5g (81%) of A2.3 HPLC YMC S-5 4.6x33mm (2min grad): retention time 2.80min, M+H4" = 403.21

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2646 - 2649
[2]Patent: WO2006/122137,2006,A1 .Location in patent: Page/Page column 82

5
[ 887147-25-3 ]
[ 914942-88-4 ]

Yield	Reaction Conditions	Operation in experiment
75 - 81%	With N-iodo-succinimide; In acetonitrile; at 0℃; for 2.25h;Cooling with ethanol-dry ice;Product distribution / selectivity;	Al.11 (8.0 g, 28.9 mmol) was dissolved in acetonitrile (260 mL) and cooled in an ice bath. N-iodosuccinimide (6.87g, 29 mmol) was added portion wise with stirring. The reaction mixture was stirred for an additional 30 min, then the solvent removed under reduced pressure. The residue was purified on silica gel column (ethyl acetate) to yield 8.73 g (75%) of A1.12. M+H + = 404.02.Alternate preparation:Al.11 (25.0 g, 90.2 mmol) was suspended in acetonitrile (700 mL) and cooled in an ice-ethanol bath. N-iodosuccinimide (NIS) (19.5g, 84.7 mmol) dissolved in acetonitrile (20OmL) was then added dropwise over 1 hr to the suspension of Al.11 while maintaining the internal reaction temperature to below 00C. After 7OmL of NIS addition, the reaction mixture became homogeneous. After complete NIS addition, the reaction mixture was stirred at 00C for an additional 15min before quenching with sodium hydrogen sulfite solution (2M, 50OmL added dropwise over lhr at 00C ). The organic layer was separated and evaporated in vacuo. The remaining aqueous layer was extracted with dichloromethane (3 x 300 mL) and the combined organics were added to the original evaporated residue and once again evaporated in vacuo. This residue was taken up in dichloromethane (500 mL) and washed with water (500 mL). The organic layer was dried (Na2SO4) and stirred with decolorizing charcoal (5g), before filtering and pre-absorbing on celite. Purification by column chromatography (dicnloromethane?ethyl acetate gradient) gave a yellow solid (31.3g) which was slurried in anhydrous methanol (40 mL), then filtered to give pure A1.12 (26.6g). The filtrate was evaporated in vacuo and the slurry/filter process repeated (2x) to give a total of 29.4g (81%) of A1.12. M+-IOO (100%) = 304.19, M++H + = 404.17, M++Na EPO <DP n="80"/>= 426.14. Eta NMR (400 MHz5 DMSO) delta: 7.97 (s, IH), 5.78 (s, 2H), 3.97 (s, 3H), 3.17 (s, 3H), 1.31 (s, 9H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2646 - 2649
[2]Patent: WO2006/122137,2006,A1 .Location in patent: Page/Page column 78; 78-79
[3]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 845 - 849

6
[ 914943-91-2 ]
[ 914942-88-4 ]
[ 914943-90-1 ]

Yield	Reaction Conditions	Operation in experiment
65%	With triethylamine;bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 20 - 90℃; for 0.833333h;	Dichlorobis(triphenylphosphine)rhoalladium (104mg, 0.145mmol) was added in one portion to a mixture of A1.12 (1.Og, 2.48mmol), <strong>[914943-91-2]3-ethynyl-benzoic acid tert-butyl ester</strong> (753mg, 3.72mmol) and triethylamine (10ml) in DMF (7.0ml) at room temperature under a nitrogen atmosphere. The resulting mixture was heated to 90 0C for 50min before cooling to room temperature and evaporating in vacuo. The residue was purified by column chromatography using ethyl acetate:hexane as eluent to give 765mg (65%) of A72.1. Found: M+H = 478.21

Reference： [1]Patent: WO2006/122137,2006,A1 .Location in patent: Page/Page column 117

7
[ 914944-24-4 ]
[ 914942-88-4 ]
[ 914944-25-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	With triethylamine;bis-triphenylphosphine-palladium(II) chloride; at 90℃; for 0.5h;	A101.3 (107mg, O.thetammol), A1.12 (164mg, 0.41 mmol) bis(triphenylphophine)palladium dichloride and triethylamine were degassed by bubbling nitrogen through the reaction for several minutes and then heated under a nitrogen atmosphere at 90 0C for 30 minutes. The mixture was concentrated under reduced pressure and the product purified by silica gel chromatography (hexane/ethyl acetate) to yield A101.4 (148mg, 80%). LCMS: Ret. Time - 3.53 min, M+it = 454.39.

Reference： [1]Patent: WO2006/122137,2006,A1 .Location in patent: Page/Page column 126

8
[ 914946-45-5 ]
[ 914942-88-4 ]
[ 914946-47-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With copper(l) iodide; diisopropylamine;bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 75℃; for 0.75h;	To a mixture of A214.5 (1.00 g, 5.74 mmol), tert~Butyl6-arnino-7-iodo-l- methyl-lH-imidazo[4,5-c]pyridin-4-yl(methyl)carbamate (1.78 g, 4.42 mmol), dichlorobis(triphenyl-phosphine)palladium II (0.186 g, 0.265 mmol), and copper EPO <DP n="162"/>iodide (0.042 g, 0.221 mmol) in anhydrous dimethylformamide (12 mL) degassed well with nitrogen was added diisopropylamine (15 mL, 0.111 mol). The reaction mixture was immersed in an oil bath at 750C and stirred for 45 min. The solvent was removed under reduced pressure, and the residue was purified by flash silica gel chromatography using a mixture of methanol in dichloromethane (5%-8%) to give 1.88 g (95%) of A214.6 as a tan solid. The compound had an HPLC retention time = 2.13 min. (Column: Chromolith SpeedROD 4.6 x 50 mm - 4 min.; Solvent A = 10% MeOH, 90% H2O, and 0.1% TFA; Solvent B = 90% MeOH, 10% H2O5 and 0.1% TFA) and a LC/MS M+1 = 450.35.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 7006 - 7012
[2]Patent: WO2006/122137,2006,A1 .Location in patent: Page/Page column 160-161

9
[ 914942-88-4 ]
[ 766-81-4 ]
[ 914943-95-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 75℃; for 0.5h;	A1.12 (201 mg, 0.5 mmol), bis(triphenyiphosphine) palladium dichloride (21mg, 0.03 mmol), <strong>[766-81-4]3-bromophenylacetylene</strong> (113 mg, 0.65 mmol) copper iodide EPO <DP n="121"/>W(4.3mg, 0,025 mmol) and diisopropylethylamine (0.2mL 1.5 mmol) were suspended in DMF (2.5mL) and degassed by bubbling a stream of nitrogen through the reaction for several minutes. The reaction was then heated to 75 0C for 30 minutes and was concentrated and purified by silica gel chromatography (hexane/ethylacetate gradient) to yield A75.1. (281 mg 123%) LCMS: RT = 3.47min M+H+ = 458.19. The material was used in the next step without further purification.

Reference： [1]Patent: WO2006/122137,2006,A1 .Location in patent: Page/Page column 119-120

10
[ 766-98-3 ]
[ 914942-88-4 ]
C₂₁H₂₂FN₅O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2646 - 2649

11
[ 914942-88-4 ]
[ 768-70-7 ]
C₂₂H₂₅N₅O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2646 - 2649

12
[ 914942-88-4 ]
[ 2561-17-3 ]
C₂₁H₂₂FN₅O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2646 - 2649

13
[ 914942-88-4 ]
[ 766-49-4 ]
C₂₁H₂₂FN₅O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2646 - 2649

14
[ 914942-88-4 ]
[ 98-86-2 ]
[ 914942-90-8 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 5316 - 5319

15
[ 914942-88-4 ]
[ 914947-28-7 ]
[ 914947-29-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 7006 - 7012

16
[ 914942-88-4 ]
[ 445468-63-3 ]
[ 1346935-15-6 ]