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[ CAS No. 1313441-88-1 ]

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Chemical Structure| 1313441-88-1
Chemical Structure| 1313441-88-1
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Product Details of [ 1313441-88-1 ]

CAS No. :1313441-88-1 MDL No. :MFCD21602848
Formula : C20H30BNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :359.27 g/mol Pubchem ID :-
Synonyms :

Safety of [ 1313441-88-1 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 UN#:
Hazard Statements:H302-H312-H332 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1313441-88-1 ]

  • Downstream synthetic route of [ 1313441-88-1 ]

[ 1313441-88-1 ] Synthesis Path-Downstream   1~15

  • 2
  • [ 360773-84-8 ]
  • [ 73183-34-3 ]
  • [ 1313441-88-1 ]
YieldReaction ConditionsOperation in experiment
87% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In dimethyl sulfoxide; at 70℃; for 12h;Inert atmosphere; A mixture of <strong>[360773-84-8]tert-butyl N-[1-(4-bromophenyl)cyclopropyl]carbamate</strong> (3 g, 9.61 mmol, CAS360773-84-8), Pin2B2 (4.88 g, 19.2 mmol), KOAc (2.83 g, 28.8 mmol) and cyclopentyl(diphenyl) phosphane; dichloromethane; dichloropalladium; iron (392 mg, 480 umol) in DMSO (30 mL) was degassed and then heated to 70 C. for 12 hours under N2. On completion, the mixture was quenched with water (200 mL) and filtered. The filter cake was purified by silica gel chromatography (SiO2) to give the title compound (3.0 g, 87% yield) as a white solid. LC-MS (ESI+) m/z 398.2 (M+K)+.
80% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In dimethyl sulfoxide; at 80℃; for 5h; Step 2: Preparation of tert-butyl {1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopropyl}carbamate A suspension of tert-butyl[1(4-bromophenyl)cyclopropyl]carbamate (400 mg) and 4,4,4',4',5,5,5',51-octamethyl-2,2'-bi-1,3,2-dioxaborolane (390 mg) and potassium acetate (377 mg) and PdCl2(dppf)CH2Cl2 (31 mg) in dimethylsulfoxide (6.5 mL) was degassed for 5 min then stirred at 80 C. for 5 h. The reaction mixture was diluted with benzene and filtered. The filtrate was washed with brine (5 times). The organics were dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by column chromatography (0-20% ethyl acetate in hexanes) gave the product (367 mg, 80%). 1HNMR (CDCl3) 400 MHz delta: 7.73 (d, J=8.3 Hz, 2H), 7.19 (d, J=8.3 Hz, 2H), 5.25 (br s, 1H), 1.47-1.18 (m, 25H).
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; In N,N-dimethyl-formamide; at 100℃; 5-tert-butyl-N-(1-[4-[2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]phenyl]cyclopropyl)-1,2,4-oxadiazole-3-carboxamide 22.6 mg (2.1% for 6 steps) was prepared from <strong>[360773-84-8]tert-butyl N-[1-(4-bromophenyl)cyclopropyl]carbamate</strong>, 4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane, 4-chloro-3-nitropyridin-2-amine and 5-tert-butyl-1,2,4-oxadiazole-3-carboxylate using Method 19R, 2J, 1G, 15P, 19T and 11N. HPLC: 99.9% purity. MS: m/z=483.1 [M+H]+. 1H NMR (400 MHz, CD3OD): delta 8.45-8.25 (m, 2H), 8.23-8.15 (m, 1H), 8.05-8.01 (m, 1H), 7.75 (s, 1H), 7.53-7.52 (m, 2H), 7.35-7.25 (m, 1H), 4.01 (s, 3H), 1.52 (s, 9H), 1.48 (s, 4H).
1.46 g With potassium acetate; palladium diacetate; XPhos; In acetonitrile; at 80℃;Inert atmosphere; Step 2: tert-butyl (l-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)cyclopropyl)carbamate: The product from Step 1 above (1.43 g, 4.50 mmol, 98% purity), b 5,-(pinacolato)diboron (1.39 g, 5.48 mmol), palladium(II) acetate (0.051 g, 0.229 mmol), X-Phos (0.219 g, 0.457 mmol) and potassium acetate (1.35 g, 13.7 mmol) were combined in a vessel, which was evacuated and purged with N2 three times. MeCN (25 ml) was added and the vessel was purged with N2 and then heated at 80 C overnight. The mixture was diluted with DCM (20 ml) and filtered through Celite, washing with DCM (3 x 20 ml). The filtrate was concentrated in vacuo and the residue was purified by column chromatography (80 g cartridge, 0-25% EtOAc/isohexane) to afford the title compound (1.46 g, 3.91 mmol, 96% purity) as a cream powder. 1H NMR (400 MHz, DMSO- ) delta 7.74 (s, 1H), 7.62 - 7.50 (m, 2H), 7.15 - 7.10 (m, 2H), 1.41 - 1.22 (m, 21H), 1.17 - 1.10 (m, 4H).
6.5 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 2-methyltetrahydrofuran; at 80℃; for 8h;Inert atmosphere; Compound B (2.4g, 7.7mmol) was dissolved in dry 2-methyltetrahydrofuran,Add bis(pinacolate) diboron (2.4g, 9.4mmol),Potassium acetate (1.5g, 15.4mmol),Pd(dppf)Cl2 (0.28g, 0.38mmol),After nitrogen substitution, the reaction was carried out at 80 degrees for 8 hours.The reaction solution was filtered through celite, and the filtrate was evaporated to dryness and washed with petroleum ether to obtain white solid product C (6.5g).That is (4-(1-((tert-butoxycarbonyl)amino)cyclopropyl)phenyl)boronic acid ester.

  • 4
  • [ 1313441-88-1 ]
  • [ 1374262-88-0 ]
  • [ 1374261-40-1 ]
  • 5
  • [ 1313441-88-1 ]
  • [ 1374262-88-0 ]
  • [ 1374263-34-9 ]
YieldReaction ConditionsOperation in experiment
74% With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; ethyl acetate; at 80℃; for 18h; Step 3: Preparation of tert-butyl {1-[4-(2-phenyl-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclopropyl}carbamate A suspension of 3-bromo-2-phenyl-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepine (50 mg) and tert-butyl {1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopropyl}carbamate (92 mg) and potassium phosphate (82 mg) and PdCl2(dppf)CH2Cl2 (11 mg) in dioxane (2.5 mL) and H2O (0.25 mL) was degassed for 5 min then stirred at 80 C. for 18 h. The reaction mixture was concentrated under reduced pressure. Purification by column chromatography (0-50% ethyl acetate in hexanes) gave the product (51 mg, 74%). 1HNMR (DMSO-d6) 400 MHz δ: 8.55 (s, 1H), 8.09-8.04 (m, 1H), 7.98-7.93 (m, 1H), 7.70 (br s, 1H), 7.48 (d, J=6.9 Hz, 2H), 7.39-7.06 (m, 10H), 6.94-6.87 (m, 1H), 6.78-6.65 (m, 1H), 1.44-1.08 (m, 13H). LCMS: 542 [M+H].
  • 6
  • [ 1313441-88-1 ]
  • [ 1431551-97-1 ]
  • C28H33Cl2FN2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,4-dioxane; water; at 80℃; for 4h;Inert atmosphere; Example 21 N-((1 R,2S)-1 -(4'-(1-aminocyclopropyl)-[1 ,1 '-biphenyl]-4-yl)-3-fluoro- 1-hydroxypropan-2-yl)-2,2-dichloroacetamideA mixture of tert-butyl (1-(4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)phenyl)cyclopropyl)carbamate (252 mg, 0.7 mmol), 2,2-dichloro-1-((4S,5R)-4- (fluoromethyl)-5-(4-iodophenyl)-2,2-dimethyloxazolidin-3-yl)ethanone (250 mg, 0.56 mmol), CS2CO3 (365 mg, 1.12 mmol) in dioxane (4 mL) and water (1 mL) is bubbled with nitrogen gas for 2 minutes. Pd(PPh3)4 (64 mg, 0.056 mmol) is added and the resulting reaction mixture heated at 80C for 4 hours. After cooling to room temperature, the reaction is diluted with water (10 ml) and extracted with ethyl acetate (3x 10 mL). Combined organic extracts are dried over Na2S04 and concentrated. Crude compound dissolved in DCM (3 mL) and stirred with TFA (0.6 mL) at room temperature for 1 hour. Reaction is diluted with toluene (10 mL) and concentrated to a syrup. Crude compound is basified slowly using saturated aq. NaHC03, saturated with NaCI, and extracted with ethyl acetate (3x 30 mL). Combined extracts dried over Na2S04 and concentrated. Solid dissolved in DMF (2 mL) and purified using HPLC eluting from 5 to 95% water/ acetonitrile to give the title compound (90 mg): 1 HNMR (400 MHz,DMSO-de) ?: 1.16-1.28 (m, 2H), 1.31 -1.41 (m, 2H), 4.15-4.36 (m, 1.5 H), 4.38- 4.47 (m, 0.5H) 4.55-4.62 (m, 0.5H), 4.65-4.74(m, 0.5H), 4.90 (bs, 1 H) 5.98 (bs, 1 H), 6.54 (bs, 1 H), 7.41-7.53 (m, 4H), 7.64 (d, 2H, J=8.0Hz), 7.72 (d, 2H, J=8.0 Hz), 8.63 (d, 1 H, J= 8Hz), 8.66-8.79 (bs, 3H), m/z (CI) 41 1 [M+1].
  • 7
  • [ 1313441-88-1 ]
  • [ 1431551-97-1 ]
  • [ 1431551-84-6 ]
  • 8
  • [ 1313441-88-1 ]
  • [ 6980-08-1 ]
  • C19H22N4O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; sodium hydrogencarbonate; In tetrahydrofuran; water; at 80℃; 5-tert-butyl-N-(1-[4-[2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]phenyl]cyclopropyl)-1,2,4-oxadiazole-3-carboxamide 22.6 mg (2.1% for 6 steps) was prepared from tert-butyl N-[1-(4-bromophenyl)cyclopropyl]carbamate, 4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane, 4-chloro-3-nitropyridin-2-amine and 5-tert-butyl-1,2,4-oxadiazole-3-carboxylate using Method 19R, 2J, 1G, 15P, 19T and 11N. HPLC: 99.9% purity. MS: m/z=483.1 [M+H]+. 1H NMR (400 MHz, CD3OD): δ 8.45-8.25 (m, 2H), 8.23-8.15 (m, 1H), 8.05-8.01 (m, 1H), 7.75 (s, 1H), 7.53-7.52 (m, 2H), 7.35-7.25 (m, 1H), 4.01 (s, 3H), 1.52 (s, 9H), 1.48 (s, 4H).
  • 9
  • [ 1313441-88-1 ]
  • tert-butyl (1-(4-(5-(2-(trans-4-(N-methylacetamido)cyclohexyl)acetamido)-3-phenylpyridin-2-yl)phenyl)cyclopropyl)carbamate [ No CAS ]
  • 10
  • [ 1313441-88-1 ]
  • tert-butyl (1-(4-(5-nitro-3-phenylpyridin-2-yl)phenyl)cyclopropyl)carbamate [ No CAS ]
  • 11
  • [ 1313441-88-1 ]
  • tert-butyl (1-(4-(5-amino-3-phenylpyridin-2-yl)phenyl)cyclopropyl)carbamate [ No CAS ]
  • 12
  • [ 1313441-88-1 ]
  • N-(trans-4-(2-((6-(4-(1-aminocyclopropyl)phenyl)-5-phenylpyridazin-3-yl)amino)-2-oxoethyl)cyclohexyl)-N-methylcyclopropanecarboxamide [ No CAS ]
  • 13
  • [ 1313441-88-1 ]
  • C37H45N5O4 [ No CAS ]
  • 14
  • [ 22353-40-8 ]
  • [ 1313441-88-1 ]
  • tert-butyl (1-(4-(3-chloro-5-nitropyridin-2-yl)phenyl)cyclopropyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
585 mg With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 50 - 60℃;Inert atmosphere; Step 3: tert-butyl (l-(4-(3-chloro-5-nitropyridin-2-yl)phenyl)cyclopropyl)carbamate: 2,3- dichloro-5-nitropyridine (505 mg, 2.62 mmol), the product from Step 2 above (941 mg, 2.52 mmol, 96% purity), ieirafc 5,-(triphenylphosphine)palladium(0) (303 mg, 0.262 mmol) and Na2C03 (694 mg, 6.55 mmol) were combined in dioxane (20 ml) and water (5 ml). The vessel was purged with N2 and heated at 50 C overnight. The mixture was diluted with water (5 ml) and heated at 60 C for 4 h. The mixture was concentrated in vacuo to remove most of the dioxane and the residue was partitioned between EtOAc (100 ml) and brine (50 ml). The phases were separated and the organic phase dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by column chromatography (40 g cartridge, 0-25% EtOAc/isohexane) to afford the title compound (585 mg, 1.43 mmol, 95% purity). 1H NMR (400 MHz, DMSO- ) delta 9.40 (d, / = 2.3 Hz, 1H), 8.86 (d, / = 2.3 Hz, 1H), 7.80 (br s, 1H, major), 7.72 (d, / = 8.4 Hz, 2H), 7.52 (br s, 1H, minor), 7.27 (d, J = 8.4 Hz, 2H), 1.41 (br s, 9H, major), 1.28 (br s, 9H, minor), 1.24 - 1.18 (m, 4H).
  • 15
  • [ 881209-27-4 ]
  • [ 1313441-88-1 ]
  • tert-butyl (1-(4-(6-amino-4-phenylpyridazin-3-yl)phenyl)cyclopropyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II) methanesulfonate; sodium carbonate; In 1,4-dioxane; water; at 90℃;Inert atmosphere; Step 1: tert-butyl (l-(4-(6-amino-4-phenylpyridazin-3-yl)phenyl)cyclopropyl)carbamate: 6- chloro-5-phenylpyridazin-3-amine (150 mg, 0.729 mmol), the product from Intermediate 10 Step 2 (262 mg, 0.729 mmol) and SPhos Precatalyst 3G (5.7 mg, 7.3 μιηο) were combined in dioxane (5 ml) and treated with 2 M Na2C03(aq) (0.821 ml, 1.641 mmol). The reaction mixture was degassed with N2 for 2 min and then heated to 90 C overnight. The mixture was cooled to RT, diluted with EtOAc (100 ml), and sequentially washed with water (100 ml) and brine (100 ml). The organic phase was dried over MgS04, filtered and concentrated in vacuo. The residue was purified by column chromatography (12 g cartridge, 0-90% EtOAc/isohexane) to afford the title compound (205 mg) as a tan solid. This material was used directly in subsequent reactions without analysis.
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