Home Cart Sign in  
Chemical Structure| 1591-38-4 Chemical Structure| 1591-38-4

Structure of 1591-38-4

Chemical Structure| 1591-38-4

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

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

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Product Citations

Shifali Shishodia ; Raymundo Nuñez ; Brayden P. Strohmier ; Karina L. Bursch ; Christopher J. Goetz ; Michael D. Olp , et al.

Abstract: PBRM1 is a subunit of the PBAF chromatin remodeling complex that uniquely contains six bromodomains. PBRM1 can operate as a tumor suppressor or tumor promoter. PBRM1 is a tumor promoter in prostate cancer, contributing to migratory and immunosuppressive phenotypes. Selective chemical probes targeting PBRM1 bromodomains are desired to elucidate the association between aberrant PBRM1 chromatin binding and cancer pathogenesis and the contributions of PBRM1 to immunotherapy. Previous PBRM1 inhibitors unselectively bind SMARCA2 and SMARCA4 bromodomains with nanomolar potency. We used our protein-detected NMR screening pipeline to screen 1968 fragments against the second PBRM1 bromodomain, identifying 17 hits with Kd values from 45 μM to >2 mM. Structure–activity relationship studies on the tightest-binding hit resulted in nanomolar inhibitors with selectivity for PBRM1 over SMARCA2 and SMARCA4. These chemical probes inhibit the association of full-length PBRM1 to acetylated histone peptides and selectively inhibit growth of a PBRM1-dependent prostate cancer cell line.

Alternative Products

Product Details of [ 1591-38-4 ]

CAS No. :1591-38-4
Formula : C8H10N2O2
M.W : 166.18
SMILES Code : O=C(N)C1=C(OC)C=CC=C1N
MDL No. :MFCD18389707
InChI Key :AQAHTARDEJNYPN-UHFFFAOYSA-N
Pubchem ID :12264814

Safety of [ 1591-38-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362

Application In Synthesis of [ 1591-38-4 ]

* 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 [ 1591-38-4 ]

[ 1591-38-4 ] Synthesis Path-Downstream   1~41

  • 1
  • [ 1591-37-3 ]
  • [ 1591-38-4 ]
YieldReaction ConditionsOperation in experiment
79% With water; potassium carbonate; In water; at 150℃; for 0.5h;Microwave irradiation; General procedure: Adapted from a literature procedure,1 the appropriate organonitrile (1.0 eq.) and K2CO3(0.2eq.)wereaddedtoamicrowavetubewithastir-barwithdeionizedwater(8.5mLpermmolsubstrate).Afterirradiationundermicrowaveat150Cfor30minutes,thereactionmixturewascooled,extractedwithEtOAc(320mL),thecombinedphasesdriedoverMgSO4andexcesssolventremovedinvacuo.TheresiduewaspurifiedbyFCC,ifrequired,togivethetitlecompound.
  • 2
  • [ 541-41-3 ]
  • [ 1591-38-4 ]
  • [ 56934-79-3 ]
  • 3
  • [ 5781-53-3 ]
  • [ 1591-38-4 ]
  • [ 54166-71-1 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 40 2'-Carbamoyl-3'-methoxyoxanilic acid methyl ester. 96 6-Amino-o-anisamide (4.98 g, 0.03 mole) is condensed with 3.04 ml. (0.033 mole) of methyl oxalyl chloride in a manner similar to example 3, giving 4.24 g of the title compound, m.p. 195-198 C., after crystallization from methanol. Elemental Analysis for C11 H12 N2 O5: Calc'd: C, 52.38; H, 4.80; N, 11.11. Found: C, 52.30; H, 4.94; H, 11.40.
EXAMPLE 23 2'-Carbamoyl-3'-methoxyoxanilic acid methyl ester. 96 6-Amino-o-anisamide (4.98 g., 0.03 mole) is condensed with 3.04 ml. (0.033 mole) of methyl oxalyl chloride in a manner similar to example 12, giving 4.24 g. of the title compound, m.p. 195-198 C., after crystallization from methanol. Elemental Analysis for C11 H12 N2 O5: Calc'd: C, 52.28; H, 4.80; N, 11.11. Found: C, 52.30; H, 4.94; H, 11.40.
EXAMPLE 23 2'-Carbamoyl-3'-methoxyoxanilic acid methyl ester. 96 6-Amino-o-anisamide (4.98 g., 0.03 mole) is condensed with 3.04 ml. (0.033 mole) of methyl oxalyl chloride in a manner similar to example 12, giving 4.24 g. of the title compound, m.p. 195-198 C., after crystallization from methanol. Elemental Analysis for C11 H12 N2 O5: Calc'd: C, 52.28; H, 4.80; N, 11.11: Found: C, 52.30; H, 4.94; H, 11.40.
EXAMPLE 23 2'-Carbamyl-3'-methoxyoxanilic acid methyl ester. 96. 6-Amino-o-anisamide (4.98 g., 0.03 mole) is condensed with 3.04 ml. (0.033 mole) of methyl oxalyl chloride in a manner similar to example 12, giving 4.24 g. of the title compound, m.p. 195-198 C., after crystallization from methanol. Elemental Analysis for C11 H12 N2 O5: Calc'd: C, 52.28; H, 4.80; N, 11.11. Found: C, 52.30; H, 4.94; H, 11.40.
EXAMPLE 40 2'-Carbamoyl-3'-methoxyoxanilic acid methyl ester. 96 6-Amino-o-anisamide (4.98 g, 0.03 mole) is condensed with 3.04 ml. (0.033 mole) of methyl oxalyl chloride in a manner similar to example 3, giving 4.24 g of the title compound, m.p. 195-198 C., after crystallization from methanol. Elemental Analysis for C11 H12 N2 O5: Calc'd: C, 52.38; H, 4.80; N, 11.11. Found: C, 52.30; H, 4.94; H, 11.40.
EXAMPLE 40 2'-Carbamoyl-3'-methoxyoxanilic acid methyl ester. 96 6-Amino-o-anisamide (4.98 g, 0.03 mole) is condensed with 3.04 ml. (0.033 mole) of methyl oxalyl chloride in a manner similar to example 3, giving 4.24 g of the title compound, m.p. 195-198C., after crystallization from methanol. Elemental Analysis for C11 H12 N2 O5: Calc'd: C, 52.38; H, 4.80; N, 11.11. Found: C, 52.30; H, 4.94; H, 11.40.

  • 4
  • [ 54166-91-5 ]
  • [ 1591-38-4 ]
  • [ 54166-72-2 ]
  • 5
  • [ 26404-20-6 ]
  • [ 1591-38-4 ]
  • [ 54166-73-3 ]
  • 6
  • [ 54166-93-7 ]
  • [ 1591-38-4 ]
  • [ 54166-86-8 ]
  • 7
  • [ 20963-23-9 ]
  • [ 1591-38-4 ]
  • [ 54166-85-7 ]
  • 8
  • [ 54166-92-6 ]
  • [ 1591-38-4 ]
  • [ 54166-84-6 ]
  • 9
  • [ 1591-38-4 ]
  • [ 4755-77-5 ]
  • [ 54249-44-4 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine; In tetrahydrofuran; at 35℃; for 2h;Cooling with ice; Step 3 (1550) To a solution of <strong>[1591-38-4]2-amino-6-methoxybenzamide</strong> (960 mg, 5.78 mmol) and triethylamine (701 mg, 6.93 mol) in THF (20 mL) was added dropwise ethyl chloroglyoxylate (868 mg, 6.36 mmol) under ice-cooling, and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was diluted with ethyl acetate, the mixture was washed with water and saturated brine, dried over sodium sulfate and concentrated under reduced pressure. The obtained concentrated residue was washed with ethanol, ethyl ((2-(aminocarbonyl)-3-methoxyphenyl)amino)(oxo)acetate to give a yellow powder (1.56 g, 100%).
EXAMPLE 34 2'-Carbamoyl-3'-methoxyoxanilic acid ethyl ester. 100/94 6-Amino-o-anisamide (8.75 g, 0.0527 mole) is condensed with 6.2 ml (0.0554 mole) of ethyl oxalyl chloride in a manner similar to example 3, giving 8.35 g of the title compound, m.p. 170-173 C., after crystallization from ethanol. Elemental Analysis for C12 H14 N2 O5: Calc'd: C, 54.13; H, 5.30; N, 10.52. Found: C, 54.36; H, 5.20; N, 10.66.
EXAMPLE 18 2'-Carbamoyl-3'-methoxyoxanilic acid ethyl ester. 100/94. 6-Amino-o-anisamide (8.75 g., 0.0527 mole) is condensed with 6.2 ml. (0.0554 mole) of ethyl oxalyl chloride in a manner similar to example 12, giving 8.35 g. of the title compound, m.p. 170-173 C., after crystallization from ethanol. Elemental Analysis for C12 H14 N2 O5: Calc'd: C, 54.13; H, 5.30; N, 10.52. Found: C, 54.36; H, 5.20; N, 10.66.
EXAMPLE 18 2'-Carbamoyl-3'-methoxyoxanilic acid ethyl ester. 100/94 6-Amino-o-anisamide (8.75 g., 0.0527 mole) is condensed with 6.2 ml. (0.0554 mole) of ethyl oxalyl chloride in a manner similar to example 12, giving 8.35 g. of the title compound, m.p. 170-173 C., after crystallization from ethanol. Elemental Analysis for C12 H14 N2 O5: Calc'd: C, 54.13; H, 5.30; N, 10.52: Found: C, 54.36; H, 5.20; N, 10.66.
EXAMPLE 18 2'-Carbamyl-3'-methoxyoxanilic acid ethyl ester. 100/94. 6-Amino-o-anisamide (8.75 g., 0.0527 mole) is condensed with 6.2 ml. (0.0554 mole) of ethyl oxalyl chloride in a manner similar to example 12, giving 8.35 g. of the title compound, m.p. 170-173 C., after crystallization from ethanol. Elemental Analysis for C12 H14 N2 O5: Calc'd: C, 54.13; H, 5.30; N, 10.52. Found: C, 54.36; H, 5.20; N, 10.66.
EXAMPLE 34 2'-Carbamoyl-3'-methoxyoxanilic acid ethyl ester. 100/94 6-Amino-o-anisamide (8.75 g, 0.0527 mole) is condensed with 6.2 ml (0.0554 mole) of ethyl oxalyl chloride in a manner similar to example 3, giving 8.35 g of the title compound, m.p. 170-173C., after crystallization from ethanol. Elemental Analysis for C12 H14 N2 O5: Calc'd: C, 54.13; H, 5.30; N, 10.52. Found: C, 54.36; H, 5.20; N, 10.66.
In pyridine; dichloromethane; EXAMPLE 1 [2-(aminocarbonyl)-3-methoxyphenylamino]oxoacetic acid ethyl ester 6-Amino-o-anisamide(8.75 g.) is condensed with 6.2 ml. of ethyl oxalyl chloride in 100 ml. methylene chloride in the presence of 9.6 ml. of pyridine at 10 C. Aqueous work-up and evaporation of the methylene chloride followed by recrystallization from ethanol gives the title compound, m.p. 170-173 C. Anal. Calcd. for C12 H14 N2 O5: C, 54.13; H, 5.30; N, 10.52. Found: C, 54.36; H, 5.20; N, 10.66. Potency: 12.5 mg/kg.

  • 10
  • [ 1591-38-4 ]
  • [ 141-75-3 ]
  • [ 56934-80-6 ]
  • 11
  • [ 1591-38-4 ]
  • [ 36239-09-5 ]
  • [ 56934-81-7 ]
  • 12
  • [ 1591-38-4 ]
  • [ 76-02-8 ]
  • [ 56934-82-8 ]
  • 13
  • [ 75-30-9 ]
  • [ 1591-38-4 ]
  • [ 81822-54-0 ]
  • 14
  • [ 1591-38-4 ]
  • [ 64470-37-7 ]
  • [ 64470-38-8 ]
  • 15
  • [ 1591-38-4 ]
  • [ 136247-88-6 ]
  • 16
  • [ 1591-37-3 ]
  • concentrated NaOH-solution [ No CAS ]
  • [ 1591-38-4 ]
  • 17
  • [ 1591-38-4 ]
  • [ 98-88-4 ]
  • [ 911469-34-6 ]
  • 18
  • [ 1591-38-4 ]
  • 5-hydroxy-2-phenyl-3<i>H</i>-quinazolin-4-one [ No CAS ]
  • 19
  • [ 1591-38-4 ]
  • [ 911469-38-0 ]
  • 20
  • [ 1591-38-4 ]
  • 4-morpholin-4-yl-2-phenyl-quinazolin-5-ol [ No CAS ]
  • 21
  • [ 1591-38-4 ]
  • [ 81822-40-4 ]
  • 22
  • [ 1591-38-4 ]
  • [ 95248-85-4 ]
  • 23
  • [ 60144-52-7 ]
  • [ 1591-38-4 ]
  • 24
  • [ 1591-38-4 ]
  • 2-Acetylamino-6-hydroxy-benzamide [ No CAS ]
  • 25
  • [ 1591-38-4 ]
  • N-acetyl-6-methoxyanthranilamide [ No CAS ]
  • 26
  • [ 1591-38-4 ]
  • [ 135106-52-4 ]
  • 27
  • [ 1591-38-4 ]
  • [ 61948-59-2 ]
  • 28
  • [ 1591-38-4 ]
  • [ 61948-86-5 ]
  • 29
  • [ 1591-38-4 ]
  • [ 858235-35-5 ]
  • 30
  • [ 1591-38-4 ]
  • 4,4'-dimethoxy-1<i>H</i>,1'<i>H</i>-[2,2']biindolylidene-3,3'-dione [ No CAS ]
  • 31
  • [ 1591-38-4 ]
  • 5-methoxy-3-[3-(3-methoxy-[2]piperidyl)-2-oxo-propyl]-3<i>H</i>-quinazolin-4-one; dihydrochloride [ No CAS ]
  • 32
  • [ 1591-38-4 ]
  • <i>N</i>2-(4-chloro-phenyl)-<i>N</i>4-(2-diethylamino-ethyl)-5-methoxy-quinazoline-2,4-diyldiamine [ No CAS ]
  • 33
  • [ 603-12-3 ]
  • [ 1591-38-4 ]
  • 37
  • [ 1591-38-4 ]
  • [ 74-88-4 ]
  • [ 56934-62-4 ]
YieldReaction ConditionsOperation in experiment
With NaH; In N-methyl-acetamide; EXAMPLE 49 3'-Methoxy-2'-N-Methylcarbamyloxanilic acid ethyl ester. 72 Slow addition of 4.98 g. (0.03 mole) of 6-amino-o-anisamide to a mixture of 57% NaH (1.32 g., 0.0315 mole) in 50 ml. dimethylformamide was carried out at room temperature. After the evolution of H2 ceased, the mixture was cooled to 3 C. and 2.06 ml. (0.033 mole) of methyliodide was slowly added at 3-5 C. The temperature was allowed to go up to room temperature and stir for 2 hours. The mixture was concentrated, the residue extracted into ethyl acetate-water, the mixture was basified, and the ethyl acetate layer was washed with water, brine and dried. Concentration gave a tan solid that was crystallized (ethanol), giving 0.45 g. (8%) of 6-amino-N-methyl-o-anisamide m.p. 186-189 C.
With NaH; In N-methyl-acetamide; EXAMPLE 49 3'-Methoxy-2'-methylcarbamoyloxanilic acid ethyl ester. 72 Slow addition of 4.98 g. (0.03 mole) of 6-amino-o-anisamide to a mixture of 57% NaH (1.32 g., 0.0315 mole) in 50 ml. dimethylformamide was carried out at room temperature. After the evolution of H2 ceased, the mixture was cooled to 3 C. and 2.06 ml. (0.033 mole) of methyliodide was slowly added at 3-5 C. The temperature was allowed to go up to room temperature and stir for 2 hours. The mixture was concentrated, the residue extracted into ethyl acetate-water, the mixture was basified, and the ethyl acetate layer was washed with water, brine and dried. Concentration gave a tan solid that was crystallized (ethanol), giving 0.45 g. (8%) Of 6-amino-N-methyl-o-anisamide m.p. 186-189 C.
With NaH; In N-methyl-acetamide; EXAMPLE 67 3'-Methoxy-2'-methylcarbamoyloxanilic acid ethyl ester. 72 Slow addition of 4.98 g. (0.03 mole) of 6-amino-o-anisamide to a mixture of 57% NaH (1.32 g., 0.0315 mole) in 50 ml. dimethylformamide was carried out at room temperature. After the evolution of H2 ceased, the mixture was cooled to 3 C. and 2.06 ml. (0.033 mole) of methyliodide was slowly added at 3-5 C. The temperature was allowed to go up to room temperature and stir for 2 hours. The mixture was concentrated, the residue extracted into ethylacetate-water, the mixture was basified, and the ethylacetate layer was washed with water, brine and dried. Concentration gave a tan solid that was crystallized (ethanol), giving 0.45 g. (8%) of 6-amino-N-methyl-o-anisamide mp. 186-189 C.
With NaH; In N-methyl-acetamide; EXAMPLE 67 3'-Methoxy-2'-methylcarbamoyloxanilic acid ethyl ester. 72 Slow addition of 4.98 g. (0.03 mole) of 6-amino-o-anisamide to a mixture of 57% NaH (1.32 g., 0.0315 mole) in 50 ml. dimethylformamide was carried out at room temperature. After the evolution of H2 ceased, the mixture was cooled at 3C. and 2.06 ml. (0.033 mole) of methyliodide was slowly added at 3-5C. The temperature was allowed to go up to room temperature and stir for 2 hours. The mixture was concentrated, the residue extracted into ethylacetate-water, the mixture was basified, and the ethylacetate layer was washed with water, brine and dried. Concentration gave a tan solid that was crystallized (ethanol), giving 0.45 g. (8%) of 6-amino-N-methyl-o-anisamide mp. 186-189C.

  • 38
  • isopropyl oxalyl chloride [ No CAS ]
  • [ 1591-38-4 ]
  • [ 54166-73-3 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 42 2'-Carbamoyl-3'-methoxyoxanilic acid isopropyl ester. 57 6-Amino-o-anisamide (4.98 g, 0.03 mole) is condensed with 4.25 ml (0.033 mole) of isopropyl oxalyl chloride in a manner similar to example 3, giving 4.74 g of the title compound, m.p. 128-132 C., after crystallization from benzene. Elemental Analysis for C13 H16 N2 O5: Calc'd: C, 55.71; H, 5.75; N, 10.00. Found: C, 55.66; H, 5.93; N, 10.38.
EXAMPLE 25 2'-Carbamoyl-3'-methoxyoxanilic acid isopropyl ester. 57 6-Amino-o-anisamide (4.98 g., 0.03 mole) is condensed with 4.25 ml. (0.033 mole) of isopropyl oxalyl chloride in a manner similar to example 12, giving 4.74 g. of the title compound, m.p. 128-132 C., after crystallization from benzene. Elemental Analysis for C13 H16 N2 O5: Calc'd: C, 55.71; H, 5.75; N, 10.00: Found: C, 55.66; H, 5.93; N, 10.38.
EXAMPLE 25 2'-Carbamoyl-3'-methoxyoxanilic acid isopropyl ester. 57 6-Amino-o-anisamide (4.98 g., 0.03 mole) is condensed with 4.25 ml. (0.033 mole) of isopropyl oxalyl chloride in a manner similar to example 12, giving 4.74 g. of the title compound, m.p. 128-132 C., after crystallization from benzene. Elemental Analysis for C13 H16 N2 O5: Calc'd: C, 55.71; H, 5.75; N, 10.00. Found: C, 55.66; H, 5.93; N, 10.38.
EXAMPLE 25 2'-Carbamyl-3'-methoxyoxanilic acid isopropyl ester. 57 6-Amino-o-anisamide (4.98 g., 0.03 mole) is condensed with 4.25 ml. (0.033 mole) of isopropyl oxalyl chloride in a manner similar to example 12, giving 4.74 g. of the title compound, m.p. 128-132 C., after crystallization from benzene. Elemental Analysis for C13 H16 N2 O5: Calc'd: C, 55.71; H, 5.75; N, 10.00. Found: C, 55.66; H, 5.93; N, 10.38.
EXAMPLE 42 2'-Carbamoyl-3'-methoxyoxanilic acid isopropyl ester. 57 6-Amino-o-anisamide (4.98 g, 0.03 mole) is condensed with 4.25 ml (0.033 mole) of isopropyl oxalyl chloride in a manner similar to example 3, giving 4.74 g of the title compound, m.p. 128-132 C., after crystallization from benzene. Elemental Analysis for C13 H16 N2 O5: Calc'd: C, 55.71; H, 5.75; N, 10.00. Found: C, 55.66; H, 5.93; N, 10.38.
EXAMPLE 42 2'-Carbamoyl-3'-methoxyoxanilic acid isopropyl ester. 57 6-Amino-o-anisamide (4.98 g, 0.03 mole) is condensed with 4.25 ml (0.033 mole) of isopropyl oxalyl chloride in a manner similar to example 3, giving 4.74 g of the title compound, m.p. 128-132C., after crystallization from benzene. Elemental Analysis for C13 H16 N2 O5: Calc'd: C, 55.71; H, 5.75; N, 10.00. Found: C, 55.66; H, 5.93; N, 10.38.

  • 39
  • n-propyl oxalyl chloride [ No CAS ]
  • [ 1591-38-4 ]
  • [ 54166-72-2 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 41 2'-Carbamoyl-3'-methoxyoxanilic acid n-propyl ester. 96 6-Amino-o-anisamide (4.98 g, 0.03 mole) is condensed with 4.25 ml (0.033 mole) of n-propyl oxalyl chloride in a manner similar to example 3, giving 4.81 g of the title compound, m.p. 158-161 C., after crystallization from acetonitrile. Elemental Analysis for C13 H16 N2 O5: Calc'd: C, 55.71; H, 5.75; N, 10.00. Found: C, 55.92; H, 5.93; N, 10.34.
EXAMPLE 24 2'-Carbamoyl-3'-methoxyoxanilic acid n-propyl ester. 96 6-Amino-o-anisamide (4.98 g., 0.03 mole) is condensed with 4.25 ml. (0.033 mole) of n-propyl oxalyl chloride in a manner similar to example 12, giving 4.81 g. of the title compound, m.p. 158-161 C., after crystallization from acetonitrile. Elemental Analysis for C13 H16 N2 O5: Calc'd: C, 55.71; H, 5.75; N, 10.00: Found: C, 55.92; H, 5.93; N, 10.34.
EXAMPLE 24 2'-Carbamoyl-3'-methoxyoxanilic acid n-propyl ester. 96 6-Amino-o-anisamide (4.98 g., 0.03 mole) is condensed with 4.25 ml. (0.033 mole) of n-propyl oxalyl chloride in a manner similar to example 12, giving 4.81 g. of the title compound, m.p. 158-161 C., after crystallization from acetonitrile. Elemental Analysis for C13 H16 N2 O5: Calc'd: C, 55.71; H, 5.75; N, 10.00. Found: C, 55.92; H, 5.93; N, 10.34.
EXAMPLE 24 2'-Carbamyl-3'-methoxyoxanilic acid n-propyl ester. 96 6-Amino-o-anisamide (4.98 g., 0.03 mole) is condensed with 4.25 ml. (0.033 mole) of n-propyl oxalyl chloride in a manner similar to example 12, giving 4.81 g. of the title compound, m.p. 158-161 C., after crystallization from acetonitrile. Elemental Analysis for C13 H16 N2 O5: Calc'd: C, 55.71; H, 5.75; N, 10.00. Found: C, 55.92; H, 5.93; N, 10.34.
EXAMPLE 41 2'-Carbamoyl-3'-methoxyoxanilic acid n-propyl ester. 96 6-Amino-o-anisamide (4.98 g, 0.03 mole) is condensed with 4.25 ml (0.033 mole) of n-propyl oxalyl chloride in a manner similar to example 3, giving 4.81 g of the title compound, m.p. 158-161 C., after crystallization from acetonitrile. Elemental Analysis for C13 H16 N2 O5: Calc'd: C, 55.71; H, 5.75; N, 10.00. Found: C, 55.92; H, 5.93; N, 10.34.
EXAMPLE 41 2'-Carbamoyl-3'-methoxyoxanilic acid n-propyl ester. 96 6-Amino-o-anisamide (4.98 g, 0.03 mole) is condensed with 4.25 ml (0.033 mole) of n-propyl oxalyl chloride in a manner similar to example 3, giving 4.81 g of the title compound, m.p. 158-161C., after crystallization from acetonitrile. Elemental Analysis for C13 H16 N2 O5: Calc'd: C, 55.71; H, 5.75; N, 10.00. Found: C, 55.92; H, 5.93; N, 10.34.

  • 40
  • [ 1591-38-4 ]
  • [ 74-88-4 ]
  • [ 56934-53-3 ]
  • [ 56934-62-4 ]
YieldReaction ConditionsOperation in experiment
With NaH; In N-methyl-acetamide; EXAMPLE 49 3'-Methoxy-2'-methylcarbamoyloxanilic acid ethyl ester. 72 Slow addition of 4.98 g. (0.03 mole) of 6-amino-o-anisamide to a mixture of 57% NaH (1.32 g., 0.0315 mole) in 50 ml. dimethylformamide was carried out at room temperature. After the evolution of H2 ceased, the mixture was cooled to 3 C. and 2.06 ml. (0.033 mole) of methyliodide was slowly added at 3-5 C. The temperature was allowed to go up to room temperature and stir for 2 hours. The mixture was concentrated, the residue extracted into ethyl acetate-water, the mixture was basified, and the ethyl acetate layer was washed with water, brine and dried. Concentration gave a tan solid that was crystallized (ethanol), giving 0.45 g (8%) Of 6-amino-N-methyl-o-anisamide m.p. 186-189 C. Elemental Analysis for C9 H12 N2 O2: Calculated: C, 59.98; H, 6.71; N, 15.55. Found: C, 60.42; H, 7.04; N, 15.42.
  • 41
  • [ 1039948-89-4 ]
  • [ 1591-38-4 ]
  • [ 1044871-20-6 ]
YieldReaction ConditionsOperation in experiment
55% With toluene-4-sulfonic acid; sodium hydrogensulfite; In N,N-dimethyl acetamide; at 115℃; for 20.0h; To a solution of 2-amino-6-methoxy-benzamide (1.00 g, 6.01 mmol) and <strong>[1039948-89-4]4-(2-hydroxy-ethoxy)-3,5-dimethyl-benzaldehyde</strong> (1.28 g, 6.59 mmol) in N,N-dimethylacetamide (15 mL) were added NaHSO3 (58.5 wt %, 0.68 g, 6.50 mmol) and p-TSA (0.23 g, 1.20 mmol) and the reaction mixture was heated at 115 C. for 20 hours, and cooled to room temperature. N,N-dimethylacetamide was removed under reduced pressure. The residue was diluted with water (50 mL), stirred for 30 minutes, and then filtered. The solid was suspended in dichloromethane (30 mL), stirred for 1 h, filtered, and dried under vacuum to give 2-[4-(2-hydroxyethoxy)-3,5-dimethylphenyl]-5-methoxy-3H-quinazolin-4-one as an off-white solid. Yield: 1.1 g (55%)
55% With toluene-4-sulfonic acid; sodium hydrogensulfite; In N,N-dimethyl acetamide; at 115℃; for 20.0h; To a solution of 2-amino-6-methoxy-benzamide (1.00 g, 6.01 mmol) and <strong>[1039948-89-4]4-(2-hydroxy-ethoxy)-3,5-dimethyl-benzaldehyde</strong> (1.28 g, 6.59 mmol) in N,N-dimethylacetamide (15 mL) were added NaHSO3 (58.5 wt %, 0.68 g, 6.50 mmol) and p-TSA (0.23 g, 1.20 mmol) and the reaction mixture was heated at 115 C. for 20 hours, and cooled to room temperature. N,N-dimethylacetamide was removed under reduced pressure. The residue was diluted with water (50 mL), stirred for 30 minutes, and then filtered. The solid was suspended in dichloromethane (30 mL), stirred for 1 h, filtered, and dried under vacuum to give 2-[4-(2-hydroxy-ethoxy)-3,5-dimethyl-phenyl]-5-methoxy-3H-quinazolin-4-one as an off-white solid. Yield: 1.1 g (55%).
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 1591-38-4 ]

Aryls

Chemical Structure| 63920-73-0

A436294 [63920-73-0]

2-Amino-4,6-dimethoxybenzamide

Similarity: 0.98

Chemical Structure| 98991-68-5

A966969 [98991-68-5]

2-Amino-3,6-dimethoxybenzamide

Similarity: 0.91

Chemical Structure| 38487-91-1

A367695 [38487-91-1]

2-Amino-4-methoxybenzamide

Similarity: 0.90

Chemical Structure| 136247-88-6

A438834 [136247-88-6]

2-Amino-6-hydroxybenzamide

Similarity: 0.90

Ethers

Chemical Structure| 63920-73-0

A436294 [63920-73-0]

2-Amino-4,6-dimethoxybenzamide

Similarity: 0.98

Chemical Structure| 98991-68-5

A966969 [98991-68-5]

2-Amino-3,6-dimethoxybenzamide

Similarity: 0.91

Chemical Structure| 38487-91-1

A367695 [38487-91-1]

2-Amino-4-methoxybenzamide

Similarity: 0.90

Amides

Chemical Structure| 63920-73-0

A436294 [63920-73-0]

2-Amino-4,6-dimethoxybenzamide

Similarity: 0.98

Chemical Structure| 98991-68-5

A966969 [98991-68-5]

2-Amino-3,6-dimethoxybenzamide

Similarity: 0.91

Chemical Structure| 38487-91-1

A367695 [38487-91-1]

2-Amino-4-methoxybenzamide

Similarity: 0.90

Chemical Structure| 136247-88-6

A438834 [136247-88-6]

2-Amino-6-hydroxybenzamide

Similarity: 0.90

Amines

Chemical Structure| 63920-73-0

A436294 [63920-73-0]

2-Amino-4,6-dimethoxybenzamide

Similarity: 0.98

Chemical Structure| 98991-68-5

A966969 [98991-68-5]

2-Amino-3,6-dimethoxybenzamide

Similarity: 0.91

Chemical Structure| 38487-91-1

A367695 [38487-91-1]

2-Amino-4-methoxybenzamide

Similarity: 0.90

Chemical Structure| 136247-88-6

A438834 [136247-88-6]

2-Amino-6-hydroxybenzamide

Similarity: 0.90