[ CAS No. 148893-10-1 ]

Name: 148893-10-1|O-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethyl uronium hexafluorophosphate|98%
Brand: Ambeed
SKU: A633512
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Quality Control of [ 148893-10-1 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 148893-10-1 ]

CAS No. :	148893-10-1	MDL No. :	MFCD00274639
Formula :	C₁₀H₁₅F₆N₆OP	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	380.23 g/mol	Pubchem ID :	9886157
Synonyms :

Safety of [ 148893-10-1 ]

Signal Word:	Danger	Class:	4.1
Precautionary Statements:	P210-P264-P271-P240-P261-P280-P305+P351+P338-P302+P352-P304+P340-P312-P362-P370+P378-P403+P233-P501	UN#:	1325
Hazard Statements:	H228-H315-H319-H335	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 148893-10-1 ]

Downstream synthetic route of [ 148893-10-1 ]

[ 148893-10-1 ] Synthesis Path-Downstream 1~24

1
[ 302964-23-4 ]
[ 148893-10-1 ]
mixed anhydride intermediate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 60℃; for 2h;	A suspension solution of 2-[[(Butylamino)carbonyl]amino]-4-methyl-5-thiazole carboxylic acid (100 mg, 0.36 mmol), and <strong>[148893-10-1]HATU</strong> (170 mg, 0.44 mmol) in DMF (3 mL) was treated with diisopropylethyl amine (62 mL, 0.44 mmol). The mixture was heated to 60 C. for 2 h, cooled, diluted with dichloromethane (12 mL), washed with 8M aq. Urea solution in 2 N aq. HCl (6 mL, 3×), 5% aq. KHCO3 solution (6 mL, 3×), dried (Na2SO4), filtered and concentrated. The residue was triturated with EtOAc-ether to obtain the mixed anhydride intermediate (102 mg, 74%) as a white solid. A 1 M solution of sodium bis(trimethylsilylamide) in THF (170,L, 0.17 mmol) was added dropwise to a stirred solution of 2,6-dichloroaniline (19.4 mg, 0.12 mmol) in THF (1 mL). After 15 min, the mixed anhydride intermediate (41.3 mg, 0.11 mmol) was added in one portion. A few drops of DMF was added and the solution was stirred for 16 h. Additional 1 M solution of sodium bis(trimethylsilylamide) (110,L) was added and the mixture was stirred for additional 2 h. The mixture was diluted with dichloromethane (4 mL) and washed with 2 N aq. HCl solution (2 mL, 3×), satd. Aq. KHCO3 solution (3×), dried (Na2SO4), filtered and concentrated. The solid was washed with hexanes (2×) and the residue was chromatographed on a silica gel column. Elution with 80% EtOAc in hexanes followed by EtOAc afforded 307 (12 mg, 27%) as a light tan solid. [0389] ?HPLC Ret Time? is the HPLC retention time under the following conditions: YMC S5 ODS 4.6×50 mm Ballastic Column, 4 min gradient starting from 100% solvent A (10% MeOH, 90% H120, 0.2% H3PO4) to 100% solvent B (90% MeOH, 10% H2O, 0.2% H3PO4), flow rate 4 mL/min, lambda=220 nM.

Reference： [1]Patent: US2004/54186,2004,A1 .Location in patent: Page 86-87; 91

2
(6S,8R)-N-{(1R)-1-[(3AS,4S,6S 7AR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-ylpropyl]-8-amino-8-methyl-4-oxo-3-[3-(trifluoromethyl)benzyl]amino}-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxamide [ No CAS ]
[ 132-60-5 ]
[ 148893-10-1 ]
[ 437758-43-5 ]

Yield	Reaction Conditions	Operation in experiment
5.6 mg (32%)	With triethanolamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;	Example 15 N-((6S,8R)-6-[({(1R)-1-[(3aS,4S,6S,7aR)-Hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]propyl}amino)carbonyl]-8-methyl-4-oxo-3-[3-(trifluoromethyl)benzyl]amino}-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidin-8-yl)-2-phenyl-4-quinolinecarboxamide To a solution of 13a (10.0 mg, 0.0166 mmol) and 2-phenyl-4-quinolinecarboxylic acid (4.6 mg, 0.018 mmol) in 1:1 THF/CH2Cl2 (1 mL) and 200 muL DMF, was added TEA (2.8 muL, 0.020 mmol) and HAtU (7.6 mg, 0.020 mmol). The mixture was stirred at rt for 2 h, then was diluted with EtOAc. The organic phase was washed with H2O, NaHCO3, and brine, dried (Na2SO4), and concentrated. The crude product was purified by flash chromatography (55% EtOAc/hexanes), followed by preparative HPLC (gradient, 50 to 100% CH3CN/H2O+0.1% TFA) to afford 5.6 mg (32%) of Example 15 as the diTFA salt. MS (ESI) 833.6 (M+H+) 855.6 (M+Na+); 831.6 (M-H+); MS (HR-ESI) calculated for C46H49BF3N6O5 (M+H+), found 833.3828.

Reference： [1]Patent: US2003/64962,2003,A1

Yield	Reaction Conditions	Operation in experiment
		The resulting residue treated with 2-Methoxycarbonylamino-3-methyl-butyric acid (60 mg, 0.343 mmol) and HATU (130 mg, 0.343 mmol), suspended in DMF (3 mL) and cooled to 0 C. DIPEA (0.272 mL, 1.56 mmol) was added dropwise. After stirring for 4 h, NaOH (5M in H2O, 0.300 mL, 1.5 mmol) was added. This mixture was stirred for 3 h then diluted with EtOAc and washed with 1 M LiOH (2*) then brine. The organic phase was dried over MgSO4, filtered and concentrated. The crude residue was then purified by HPLC to afford the title compound (53 mg, 44%). MS (ESI) m/z 773 [M+H]+.

4
[ 201740-78-5 ]
[ 148893-10-1 ]
C₁₂⁽¹³⁾CH₁₇N₅O₄ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 9024 - 9031

5
[ 148893-10-1 ]
[ 100-51-6 ]
[ 1420476-91-0 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 642 - 645

6
[ 148893-10-1 ]
[ 71-36-3 ]
[ 1420476-92-1 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 642 - 645

7
[ 619-73-8 ]
[ 148893-10-1 ]
[ 353262-26-7 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 642 - 645

8
[ 1382486-58-9 ]
[ 148893-10-1 ]
[ 1382486-65-8 ]

Yield	Reaction Conditions	Operation in experiment
2.3 g	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 0.5h;	Method 65 Synthesis of 5-[1-(4-bromophenyl)-1,2-dimethyl-propyl]-3-(3-pyridyl)-1,2,4-oxadiazole (Intermediate 100) To a solution of I-52 (2.0 g, 7.37 mmol) in DMF (50 mL) is added <strong>[148893-10-1]HATU</strong> (4.18 g, 11.0 mmol) followed by DIEA (3.36 g, 26.0 mmol) and the solution is stirred at room temperature for 30 minutes. The reaction mixture is diluted with EtOAc, washed with water, and dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue is purified by flash chromatography (SiO2, 0-50% EtOAc/hexanes) to give I-101 (2.3 g). To a solution of I-101 (26.0 mg, 0.067 mmol) in THF (1 mL) is added I-99.1 (12.3 mg, 0.090 mmol) and PS-BEMP (55.0 mg, 0.110 mmol) and heated in the microwave at 120 C. for 30 min. The mixture is filtered, concentrated in vacuo, and purified by flash chromatography (SiO2, EtOAc/hexanes) to give I-102 (18 mg).

Reference： [1]Patent: US2013/196967,2013,A1 .Location in patent: Paragraph 0362; 0363

9
[ 55-22-1 ]
C₁₂₆H₈₁Fe₂N₁₅⁽⁴⁺⁾*4C₂F₆NO₄S₂^(1-) [ No CAS ]
[ 148893-10-1 ]
C₁₄₄H₉₀Fe₂N₁₈O₃⁽⁴⁺⁾*4F₆P^(1-) [ No CAS ]