532391-89-2|4-Methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylic acid| Ambeed

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Quality Control of [ 532391-89-2 ] Purity: 97% SDS Specification

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Product Details of [ 532391-89-2 ]

CAS No. :	532391-89-2
Formula :	C₁₀H₁₁NO₃
M.W :	193.20
SMILES Code :	O=C(C1=CC=C2C(OCCN2C)=C1)O
MDL No. :	MFCD02682041
InChI Key :	XWYHWMDBIRZPFG-UHFFFAOYSA-N
Pubchem ID :	2795296

Safety of [ 532391-89-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 532391-89-2 ]

* 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 [ 532391-89-2 ]

[ 532391-89-2 ] Synthesis Path-Downstream 1~20

1
[ 532391-89-2 ]
[ 115279-73-7 ]
[ 1067189-54-1 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In 1,4-dioxane; at 20℃; for 72.0h;	A solution of l-(4-amino-phenyl)-cyclopentanecarbonitrile (70.0 mg; 0.38 mmol), prepared as in 3(B), HOBt (76.0 mg; 0.56 mmol), EDC (108 mg; 0,56 mmol), TEA (130 uL; 0,94 mmol) and 4-methyl-3,4-dihydro-2H-l,4-benzoxazine-7-carboxylic acid (80 mg; 0.41 mmol) in DCM (10 mL) was stirred at room temperature for 72 hours. After this time, the reaction was diluted with DCM, washed with 5% NaHCO3 and then with water. The organic phase was dried (Na2SO4), filtered and evaporated to dryness. The residue was purified by preparative HPLC (Method Q) to afford the title compound as a dark oil (15.0 mg; 11%).1H NMR (300 MHz, CDC13) delta(ppm): 7.66 (br. s., 1 H), 7.58-7.63 (m, 2 H), 7.36-7.44 (m, 3 H), 7.27 (d, 1 H), 6.65 (d, 1 H), 4.25-4.30 (m, 2 H), 3.32-3.42 (m, 2 H), 2.97 (s, 3 H), 2.36-2.48 (m, 2 H), 1.82-2.15 (m, 6 H). LCMS (RT): 3.09 min (Method H); MS (ES+) gave m/z: 362.2 (MH+).

References: [1]Patent: WO2008/117175,2008,A2 .Location in patent: Page/Page column 105-106.

2
[ 532391-89-2 ]
5-(2,6-Dimethyl-phenyl)-[1,3,4]thiadiazol-2-ylamine [ No CAS ]
[ 1186388-75-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4292 - 4295.

3
[ 532391-89-2 ]
dibenzyl (3-ethoxy-5-(5-((((R)-2-((R)-1-(N-hydroxyformamido)propyl)heptanamido)methyl)carbamoyl)furan-2-yl)phenyl)phosphonate [ No CAS ]
dibenzyl (3-ethoxy-5-(5-((((R)-2-((R)-1-(N-((4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carbonyl)oxy)formamido)propyl)heptanamido)methyl)carbamoyl)furan-2-yl)phenyl)phosphonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%		INTERMEDIATE 73: dibenzyl (3-ethoxy-5-(5-((((R)-2-((R)-1-(N-((4-methyl-3,4-dihydro- 2H-benzo[b][1 ,4]oxazine-7- carbonyl)oxy)formamido)propyl)heptanamido)methyl)carbamoyl)furan-2- yl)phenyl)phosphonate Methanesulfonyl chloride (0.023 mL, 0.300 mmol) was added to a solution of 4-methyl-3,4- dihydro-2H-benzo[b][1 ,4]oxazine-7-carboxylic acid (0.053 g, 0.273 mmol) and 1- methylimidazole (0.043 mL, 0.545 mmol) in DCM (1.5 mL) at 0 C . The reaction was stirred at 0 C for 10 mins and then at RT for 20 mins. The reaction was cooled down in an ice bath again and, dibenzyl (3-ethoxy-5-(5-((((R)-2-((R)-1-(N- hydroxyformamido)propyl)heptanamido)methyl)carbamoyl)furan-2-yl)phenyl)phosphonate (0.2 g, 0.273 mmol) was added and the reaction was stirred at RT overnight. Water was added and the reaction was partitioned between water and DCM. The organic layer was passed through a hydrophobic cartridge and concentrated. Purification by Si (0-100% EtOAc/Hex) afforded the title compound as a colorless solid. (116 mg, 47 % yield). MS (m/z) 909.4 (M+H)+

References: [1]Patent: WO2017/6296,2017,A1 .Location in patent: Page/Page column 154.

4
C₁₁H₁₃NO₃ [ No CAS ]
[ 532391-89-2 ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 130,p. 73 - 85.

5
[ 532391-89-2 ]
N-(4-acetylphenyl)-4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 130,p. 73 - 85.

6
[ 532391-89-2 ]
N-{4-[1-(2-carbamimidoylhydrazono)ethyl]phenyl}-4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 130,p. 73 - 85.

7
[ 532391-89-2 ]
C₁₀H₁₀ClNO₂ [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2017,vol. 130,p. 73 - 85.

8
[ 532391-89-2 ]
20'-aminovinblastine [ No CAS ]
C₅₆H₆₈N₆O₁₀ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 7591 - 7604.

9
[ 532391-89-2 ]
tert-butyl ((S)-2-hydroxy-3-(3-(methylsulfonyl)phenoxy)propyl)(1-oxa-8-azaspiro[4.5]decan-3-yl)carbamate [ No CAS ]
tert-butyl ((S)-2-hydroxy-3-(3-(methylsulfonyl)phenoxy)propyl)(8-(4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carbonyl)-1-oxa-8-azaspiro[4.5]decan-3-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 70℃; for 16.0h;	ferf-Butyl ((5)-2-hydroxy-3-(3-(methylsulfonyl)phenoxy)propyl)(l-oxa-8-azaspiro[4.5]decan- 3-yl)carbamate (15 mg, 30.95 muiotaetaomicron), 4-methyl-3,4-dihydro-2 /-benzo[b][l,4]oxazine-7-carboxylic acid (7.18 mg, 37.14 muiotaetaomicron), HATU (14.12 mg, 37.14 muiotaetaomicron) and triethylamine in DMF (1M, 61.91 mu,, 61.91 muiotaetaomicron) solution were added in 5mL scintillation vial following by addition of DMF (1 mL). The reaction mixture was heated at 70 C for 16 h. The reaction mixture was filtered and purified by mass direct pre-HPLC. The collected fractions were lyophilized to give the title compound. LCMS m/z = 660.6 [M+H]+.

References: [1]Patent: WO2017/214002,2017,A1 .Location in patent: Page/Page column 149; 150.

10
[ 532391-89-2 ]
tert-butyl ((S)-2-hydroxy-3-(3-(methylsulfonyl)phenoxy)propyl)(1-oxa-8-azaspiro[4.5]decan-3-yl)carbamate [ No CAS ]
(3-((S)-2-hydroxy-3-(3-(methylsulfonyl)phenoxy)propylamino)-1-oxa-8-azaspiro[4.5]decan-8-yl)(4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)methanone hydrochloride [ No CAS ]

References: [1]Patent: WO2017/214002,2017,A1 .

11
[ 532391-89-2 ]
[ 771-61-9 ]
pentafluorophenyl 4-methyl-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With dicyclohexyl-carbodiimide; In 1,4-dioxane; for 17.0h;	Dicyclohexylcarbodiimide (807 mg, 3.91 mmol) was added to a stirred suspension of4-methyl-3,4-dihydro-2H-1 ,4-benzoxazine-7-carbcxylic acid (CAS 532391-89-2) (685 mg,3.55 mmcl) and pentafluorophenol (653 mg, 3.55 mmcl) in 1,4-dioxane (15 mL). Stirring was continued for 17 h by which time a colorless precipitate had formed. The mixture was filtered and evaporated; the residue was dissolved in CH2CI2 (20 mL) and evaporated to give the crude ester pentafluorophenyl 4-methyl-3,4-dihydro-2H-1 ,4-benzoxazine-7-carboxylate(1.4g, 3.90 mmcl, 100%) as a yellow oily solid which was used in the next step without purification. 1Pr2NEt (523 pL, 388 mg, 3 mmol) was added to a stirred mixture of 1-(3- brcmophenyl)ethanone (199 mg, 1 mmcl) and MgBr2Et2O (646 mg, 2.5 mmcl) in CH2CI2 (10 mL). The resulting suspension was stirred for 15 mm, then pentafluorophenyl 4-methyl-3,4- dihydro-2H-1 ,4-benzcxazine-7-carboxylate (431 mg, 1 .2 mmcl) in CH2CI2 (2 mL) was addeddropwise. After 24 h 1-(3-brcmophenyl)ethanone (199 mg, 1 mmcl), MgBr2Et2O (646 mg,2.5 mmcl), and 1Pr2NEt (523 pL, 388 mg, 3 mmcl) were added and the stirring was continued for further 24 h. 1 N phosphate buffer pH 6 (20 mL) was added, stirred for 10 mm, the organic phase was separated, the aqueous phase was extracted with CHCI3 (10 mL), the combined organic extract was washed with saturated NaHCO3 solution, brine, dried over Na2SO4 andconcentrated in vacuo. The residue was purified by flash chromatography on silica gel (n-hexane/chlcrofcrm =1:1, Rf 0.15) to afford 362 mg of crude product as yellow foam which was used in the next step without further purification. To a solution of crude 1-(3- brcmcphenyl)-3-(4-methyl-3,4-dihydrc-2H- 1 ,4-benzcxazin-7-yl )prcpane-1 ,3-dicne (362 mg) in EtDH (10 mL) hydrazine monohydrate (194 pL, 200 mg, 4 mmcl) was added. The reactionmixture was stirred at 78 00 for 15 h, cooled down to room temperature, the solvent and excess of hydrazine monchydrate were removed on the rotary evaporator. Tcluene (20 mL) was added and the mixture was concentrated to dryness. The crude product (380 mg) waspurified by flash chromatography on silica gel (chloroform/methanol =100:1, Rf 0.26) to afford the product (30 mg, 0.08 mmol, 8% over three steps) as a white solid.

References: [1]Patent: WO2018/206778,2018,A1 .Location in patent: Page/Page column 44; 59; 60.

12
[ 532391-89-2 ]
7-[5-(3-bromophenyl)-1H-pyrazol-3-yl]-4-methyl-3,4-dihydro-2H-1,4-benzoxazine [ No CAS ]

References: [1]Patent: WO2018/206778,2018,A1 .

13
[ 532391-89-2 ]
1-(3-bromophenyl)-3-(4-methyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)propane-1,3-dione [ No CAS ]

References: [1]Patent: WO2018/206778,2018,A1 .

14
[ 532391-89-2 ]
[ 99281-88-6 ]
(E)-methyl 4-(4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxamido)but-2-enoate [ No CAS ]

References: [1]Journal of the American Chemical Society,2020,vol. 141,p. 2703 - 2712.

15
[ 532391-89-2 ]
[ 6638-79-5 ]
N-methoxy-N,4-dimethyl-3,4-dihydro-2H-1,4-benzoxazine-7-carboxamide [ No CAS ]