112029-98-8|(1-Methyl-1H-pyrazol-4-yl)methanol| Ambeed

Structure of 112029-98-8

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Quality Control of [ 112029-98-8 ] Purity: 97% SDS Specification

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Product Details of [ 112029-98-8 ]

CAS No. :	112029-98-8
Formula :	C₅H₈N₂O
M.W :	112.13
SMILES Code :	CN1C=C(CO)C=N1
MDL No. :	MFCD01822311
InChI Key :	QSXREDPBMQKKAY-UHFFFAOYSA-N
Pubchem ID :	11961423

Safety of [ 112029-98-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 112029-98-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	8
Num. arom. heavy atoms	5
Fraction Csp3	0.4
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	29.62
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	38.05 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.17
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	-0.65
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-0.24
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.	-0.53
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	0.19
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	-0.01

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.52
Solubility	33.7 mg/ml ; 0.3 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.	0.32
Solubility	237.0 mg/ml ; 2.11 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Highly 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	-0.57
Solubility	30.4 mg/ml ; 0.271 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	No
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.	-7.45 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	1.0
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)	1.12

Application In Synthesis of [ 112029-98-8 ]

* 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 [ 112029-98-8 ]

[ 112029-98-8 ] Synthesis Path-Downstream 1~35

1
[ 98-91-9 ]
[ 112029-98-8 ]
[ 163008-92-2 ]

References: [1]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 465 - 475.

2
[ 112029-98-8 ]
(6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-hydroxyimino]-acetylamino}-3-(1-methyl-1H-pyrazol-4-ylmethylsulfanyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 465 - 475.

3
[ 112029-98-8 ]
diphenylmethyl 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-(trityloxyimino)acetamido]-3-[(1-methylpyrazol-4-yl)methylthio]-3-cephem-4-carboxylate [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 465 - 475.

5
[ 100852-80-0 ]
[ 112029-98-8 ]

Yield	Reaction Conditions	Operation in experiment
		Example 1.4Methyldiazolyl Methanol; Diethyl pyrazoledicarboxylate (2.0 g, 9.42 mmol) in THF at 0° C. was added NaH (60percent in mineral oil, 0.42 g, 10.37 mmol) portionwise. he resulting mixture was warmed to r.t. and stirred overnight. The reaction was quenched with saturated aqueous NH4Cl carefully. The mixture was diluted with EtOAc, separated, and extracted with EtOAc twice. The combined organic layers was dried over Na2SO4, concentrated, and purified by flash chromatography to afford the product as a colorless oil.The above diester (1.0 g, 4.42 mmol) was dissolved in MeOH, a solution of KOH in MeOH (0.28 g of KOH in 2.5 mL of MeOH) was added, and the mixture was stirred at r.t. for 24 h. After removal of solvent under reduced pressure at low temperature, the residue was dissolved in water and neutralized with aqueous HCl (1M solution). Extraction of the mixture with CHCl3 three times afforded the crude product after concentration of the combined organic layers. Without further purification the crude above product was heated to 210° C. for 30 min. to provide a dark brown oil, which was purified by flash chromatography to give the ester.The ester was reduced to corresponding alcohol by LAH. 1H-NMR: (300 MHz, CDCl3), delta: 7.32 (s, 1H); 6.25 (s, 1H); 4.68 (s, 2H); 3.88 (s, 3H); 2.74 (br, 1H).

References: [1]Patent: US2008/125467,2008,A1 .Location in patent: Page/Page column 20.

6
[ 25016-11-9 ]
[ 112029-98-8 ]

Yield	Reaction Conditions	Operation in experiment
97%		The compound of formula IX (3.48 g, 31.6 mmol) was dissolved in methanol (25 ml_) and sodium borohydride (2.50 g, 66.1 mmol, 2.09 equiv.) was added portion-wise with vigorous gas evolution. After stirring for 3 hours at room temperature, the reaction was cooled to 0 0C and slowly acidified to pH ~ 1 with 4N aqueous hydrochloric acid (20 ml_) over 55 minutes. A thick white slurry formed and this was stirred one hour at room temperature. The reaction was then basified by the gradual addition of saturated aqueous potassium carbonate solution (53.4 wtpercent K2CU3, 6.04 M; 10 ml_). This resulted in a clear, colorless solution (pH = 1.1), which was diluted with additional saturated potassium carbonate solution (200 ml_) and was extracted with ethyl acetate (2 x 200 ml_). The ethyl acetate extracts were combined, dried over sodium sulfate, filtered and concentrated to yield the compound of formula X as a light yellow oil (3.44 g, 97percent yield).
60.5%	With methanol; sodium tetrahydroborate; at 0 - 20℃; for 1h;	Step A (1-methyl-1,1-pyrazol-4-yl)methanol To a solution of 1-methyl-1H-pyrazole-4-carbaldehyde (0.500 g, 4.54 mmol) in methanol (10 mL, 200 mmol) at 0° C. was added sodium tetrahydroboride (0.515 g, 13.6 mmol). The reaction was stirred at room temperature for 1 h, and then quenched with brine, and extracted with ethyl acetate (EtOAc) (3*). The combined organic phases were washed with water, brine, dried over Na2SO4, and concentrated to give 0.308 g (60.5percent yield) of the final product as colorless oil, which was used directly for the next step without further purification. LC/MS found: 113.1 (M+1)+.
400 mg	With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃; for 2h;Cooling with ice;	Intermediate 69 (600mg, 1 eq.) was dissolved in tetrahydrofuran, and lithium aluminum hydride (210 mg, 1 eq.) was added under ice bath and the mixture was reacted at room temperature for 2 h. After completion of the reaction, 210 mul of water, 210 mul of 10percent aqueous sodium hydroxide solution, and 630 mul of water were successively added, followed by addition of anhydrous magnesium sulfate. The mixture was stirred for a while, filtered and evaporated to dryness to give 400 mg of an oil. MS (ESI): 113(M+H)

References: [1]Patent: WO2008/153870,2008,A1 .Location in patent: Page/Page column 30.
[2]Journal of Medicinal Chemistry,2008,vol. 51,p. 3777 - 3787.
[3]Russian Journal of General Chemistry,2010,vol. 80,p. 1001 - 1003.
[4]Patent: US2013/96144,2013,A1 .Location in patent: Paragraph 0174.
[5]Patent: EP3239135,2017,A1 .Location in patent: Paragraph 0132; 0133.

7
[ 112029-98-8 ]
[ 735241-98-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With thionyl chloride; In dichloromethane; at 0 - 20℃; for 3h;	To a solution of <strong>[112029-98-8](1-methyl-1H-pyrazol-4-yl)methanol</strong> (1.29 g, 11.5 mmol) (prepared from Intermediate 3 Step A) in methylene chloride (4 mL) at 0° C. was added thionyl chloride (4 mL, 50 mmol). The solution was stirred at room temperature for 3 h. Concentration under reduced pressure gave 1.50 g (100percent yield) of the desired product as white solid, which was used for the next step directly.
86%	With thionyl chloride; In dichloromethane; toluene; at 20℃; for 1h;	Into a solution of <strong>[112029-98-8](1-methyl-1H-pyrazol-4-yl)methanol</strong> (790 mg, 7.04 mmol) in DCM (2.6 mL) was added a solution of thionyl chloride (1.28 mL, 17.6 mmol) in toluene (3.50 mL) drop wise. The reaction mixture was then stirred at rt for lh. Upon completion, the reaction mixture was concentrated to afford the titled compound as an off white solid (790 mg, 86percent). 1H NMR (400 MHz, CDC13) delta 7.78 (s, 1H), 7.63 (s, 1H), 4.56 (s, 2H), 4.17 (s, 3H).
	With thionyl chloride; In dichloromethane; touluene; at 20℃; for 1h;	D604-(Chloromethyl)-l-methyI-lH-pyrazoleTo a solution of (1 -Methyl- lH-pyrazol-4-yI)methanoI (1.1 g, 9.81 mmol) indichloromethane (5.00 ml) was added thionyl chloride (2.0 ml, 27.4 mmol) in toluene (5.0 mL) dropwise. The reaction mixture was stirred for 1 hr at rt, concentrated to afford the title product (1.34 g) as a white solid, which was used in next reaction without purification.

With thionyl chloride; In dichloromethane; for 1h;Cooling with ice;

Intermediate 70 (160mg, 1 eq.) was dissolved in re-distilled dichloromethane, and dichlorosulfoxide (310 mul, 3 eq.) was added under ice bath. The mixture was reacted for 1 h, evaporated to remove solvent. The product was directly used in the next step without purification

References: [1]Patent: US2013/96144,2013,A1 .Location in patent: Paragraph 0179; 0180.
[2]Patent: WO2018/89786,2018,A1 .Location in patent: Paragraph 00396.
[3]Journal of Medicinal Chemistry,2008,vol. 51,p. 3777 - 3787.
[4]Patent: WO2012/75917,2012,A1 .Location in patent: Page/Page column 37.
[5]Patent: EP3239135,2017,A1 .Location in patent: Paragraph 0134; 0135.

8
[ 112029-98-8 ]
[ 154312-86-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	With thionyl chloride; In dichloromethane; at 25 - 30℃; for 2h;Inert atmosphere; Cooling;	To a cooled solution of <strong>[112029-98-8](1-methyl-1H-pyrazol-4-yl)-methanol</strong> (8.61 g, 0.076 mole) in DCM (100 mL) under N2 atmosphere, thionyl chloride (8.7 mL, 0.12 mole) was added drop wise. The reaction mixture was warmed to RT and stirred for 2 hours. The reaction mixture was concentrated under vacuum at 23 ? 25 °C to obtain the titlecompound.Yield: 12.77 g (99 percent); ?H - NMR (DMSO-d6, 400 MHz) oe ppm: 3.85 (s, 3H), 4.67 (s, 2H), 4.76 - 4.79 (t, 1H), 4.88 (bs, 1H), 7.47 (s, 1H), 7.78 (s, 1H).
	With thionyl chloride; In dichloromethane; at 0 - 20℃; for 2h;	The compound of formula X (0.201 g, 1.80 mmol) > was dissolved in anhydrous dichloromethane (3 mL) and thionyl chloride (0.140 <n="32"/>ITiL, 1.92 mmol, 1.06 equiv.) was added drop-wise at 0 0C. The reaction was stirred 1 hour at 0 0C and then 1 hour at room temperature. The reaction was then concentrated at 50 0C and dried under vacuum for 2 hours to yield a white solid (0.286 g). This solid was suspended in anhydrous acetonitrile and triethylamine (0.750 ml_, 5.38 mmol, 2.99 equiv.) was added. After stirring for a few minutes, tetraethylammonium cyanide (1.08 g, 6.90 mmol, 3.84 equiv.) was added in one portion. The reaction was stirred 18 hours at room temperature and was then diluted with water (15 ml_) and extracted with ethyl acetate (3 x 20 ml_). The extracts were combined, washed with saturated aqueous sodium chloride, dried over sodium sulfate, filtered and concentrated to yield a yellow oil (0.128 g). Purification by chromatography, eluting with 5percent methanol- dichloromethane, yielded the compound of formula Xl as a yellow oil (0.063 g, 30percent yield).

References: [1]Patent: WO2017/42643,2017,A1 .Location in patent: Page/Page column 22; 23.
[2]Patent: WO2008/153870,2008,A1 .Location in patent: Page/Page column 30-31.

9
[ 1259878-80-2 ]
[ 112029-98-8 ]
[ 1259877-18-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In 1,4-dioxane; at 20℃; for 18h;	EXAMPLE 7: Synthesis of 5-amino-4-(5-methylfuran-2-yl)-2-(1-rnethyl-1 H-pyrazol-4- ylmethoxy)thieno[2,3-d]pyrimidine-6-carboxamide (no. 24); 58 mg (0.52 mmol) of (1-methyl-1H-pyrazole)methanol and 72.6 mg (0.647 mmol) of potassium tert-butoxide were added to a slurry of 145 mg (0.43 mmol) of 5-amino-2- methanesulfinyl-4-(5-methylfuran-2-yl)thieno[2,3-d]pyrimidine-6-carboxamide in 3 ml of dioxane, and the mixture was stirred at room temperature for 18 hours. Water was added to the reaction mixture, which was then filtered with suction. The residue was washed with water, dried in vacuum and chromatographed on a silica-gel column with dichloromethane/ methanol as eluent, giving 5-amino-4-(5-methylfuran-2-yl)-2-(1-methyl-1 H-pyrazol-4-yl- methoxy)thieno[2,3-d]pyrimidine-6-carboxamide as orange crystals; HPLC-MS: [M+H] 385. 1H-NMR (d6-DMSO): delta [ppm] = 2.50 (s, 3H), 3.81 (s, 3H), 5.34 (s, 2H), 6.50 (d, J = 3.4 Hz, 1 H), 7.16 (bs, 2H), 7.45 (bs, 2H), 7.51 (d, J = 3.4 Hz, 1 H), 7.53 (s, 1 H), 7.80 (s, 1 H)

References: [1]Patent: WO2010/149257,2010,A1 .Location in patent: Page/Page column 76-77.

10
[ 112029-98-8 ]
[ 1381791-44-1 ]

References: [1]Patent: WO2012/75917,2012,A1 .

11
[ 112029-98-8 ]
[ 1381791-45-2 ]

References: [1]Patent: WO2012/75917,2012,A1 .

12
[ 695-34-1 ]
[ 119072-55-8 ]
[ 112029-98-8 ]
[ 1415980-87-8 ]

Yield	Reaction Conditions	Operation in experiment
84%		General procedure: To the solution of alcohol 4b (0.50 g, 2.67 mmol) and DMSO (0.41 g, 5.34 mmol) in ethyl acetate (5 ml) was added ®T3P (1.84 g, 6.68 mmol, 2.5 equiv, 50percent solution in ethyl acetate) at 0 °C. The resulting mixture was allowed to warm to RT and stirred for 1 h. Pyrazine-2-amine 3a (0.254 g, 2.67 mmol) was added to the above mixture and stirred for 15 min, which was followed by the addition of isocyanide 1c (0.33 g, 4.01 mmol) at room temperature and stirring for 4 h. Progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was diluted with ethyl acetate and neutralized with aqueous sodium bicarbonate solution. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (25 mL × 2), the combined organic phases were washed with water, brine solution, dried over anhydrous sodium sulfate, and concentrated under vacuum to afford a crude product, which was purified on silica gel using ethyl acetate and petroleum ether.

References: [1]Tetrahedron Letters,2013,vol. 54,p. 95 - 100.

13
[ 112029-98-8 ]
[ 1430057-85-4 ]