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CAS No. : | 5699-41-2 | MDL No. : | MFCD10024834 |
Formula : | C6H14N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 130.19 | Pubchem ID : | - |
Synonyms : |
NAP
|
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P260-P264-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P405-P501 | UN#: | 2735 |
Hazard Statements: | H314 | Packing Group: | Ⅲ |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ethanol; hydrazine hydrate |
Yield | Reaction Conditions | Operation in experiment |
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With ethanol |
Yield | Reaction Conditions | Operation in experiment |
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In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
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In water |
Yield | Reaction Conditions | Operation in experiment |
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With triethylamine In chloroform |
Yield | Reaction Conditions | Operation in experiment |
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In methanol |
Yield | Reaction Conditions | Operation in experiment |
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56% | With water for 24h; Reflux; | |
850 g | for 384h; | |
at 100℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
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With hydrogen In methanol |
Yield | Reaction Conditions | Operation in experiment |
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With sodium hydroxide In ethanol |
Yield | Reaction Conditions | Operation in experiment |
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14.5 g | With hydrogen In ethanol; acetic acid at 30℃; |
Yield | Reaction Conditions | Operation in experiment |
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In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With hydrogenchloride; triethylamine 1) DMF, a) 10 h, 21 deg C, b) 5 h, 60 deg C, 2) H2O; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With nickel In toluene for 6.5h; Heating; | |
In benzene for 7h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 32% 2: 48% | In chloroform for 6h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 65% 2: 28% | at 100℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 14.5 g / H2 / PtO2 / acetic acid; ethanol / 30 °C 2: 16.5 g / diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 14.5 g / H2 / PtO2 / acetic acid; ethanol / 30 °C 2: 16.5 g / diethyl ether 3: 14 g / 22percent H2O2, Na2WO4*2H2O, Trilon B / H2O |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: CH2Cl2 2: NaBH4 3: 70 percent / H2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: CH2Cl2 2: NaBH4 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 96 percent 2: 30 percent / pyridine / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Et3N / CHCl3 2: (i) NaOH, nPrOH, (ii) /BRN= 972409/, Et3N, benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: Et3N / CHCl3 2: (i) NaOH, nPrOH, (ii) /BRN= 972409/, Et3N, benzene 3: AcOH |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: Et3N / CHCl3 2: (i) NaOH, nPrOH, (ii) /BRN= 972409/, Et3N, benzene 3: AcOH 4: (i) NaOH, EtOH, CH2Cl2, (ii) /BRN= 1882498/, Et3N |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: Et3N / CHCl3 2: (i) NaOH, nPrOH, (ii) /BRN= 972409/, Et3N, benzene 3: AcOH 4: (i) NaOH, EtOH, CH2Cl2, (ii) /BRN= 1882498/, Et3N 5: tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: CH2Cl2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: CH2Cl2 3: aq. Ba(OH)2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: methanol 2: (i) MeCN, (ii) aq. NaOH |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | 30 N-acetyl-N'-{N-[(2S,3S)-3-trans-ethoxycarbonyloxirane-2-carbonyl]-L-phenylalanyl}-1,4-diaminobutane N-[(2S,3S)-3-trans-ethoxycarbonyloxirane-2-carbonyl]-L-phenylalanine (1.22 g) and N-acetyl-1,4-diaminobutane (0.47 g) were condensed together in the same manner as in Example 20 to yield the title compound (compound 28; 0.96 g) as a white powder (yield 63%). Elemental analysis (for C21 H29 N3 O6*0.3 H2 O): Calculated: C; 59.37, H; 7.02, N; 9.89 Found: C; 59.37, H; 6.89, N; 9.79 1 H NMR δ ppm (DMSO-d6) 1.22 (3H, t, J=7.0 Hz), 1.32 (4H, m), 1.78 (3H, s), 2.79 (1H, dd, J=9.5, 14.0 Hz), 2.92-3.10 (5H, m), 3.42 (1H, d, J=2.0 Hz), 3.64 (1H, d, J=2.0 Hz), 4.17 (2H, m), 4.50 (1H, m), 7.16-7.31 (5H, m), 7.79 (1H, br t, J=5.5 Hz), 8.11 (1H, br t, J=5.5 Hz), 8.66 (1H, br d, J=8.5 Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane | 4 3,4-Dihydro-6-[N-(4-acetylaminobutyl)sulfamoyl]-3-(2-chlorophenyl)-2-methyl-4-oxothieno[2,3-d]pyrimidine EXAMPLE 4 3,4-Dihydro-6-[N-(4-acetylaminobutyl)sulfamoyl]-3-(2-chlorophenyl)-2-methyl-4-oxothieno[2,3-d]pyrimidine To 8.0 g of 3,4-dihydro-3-(2-chlorophenyl)-6-chlorosulfonyl-2-methyl-4-oxothieno[2,3-d]pyrimidine were added 150 ml of dichloromethane, 3.3 g of 4-acetylaminobutylamine and 5.9 ml of triethylamine, and the mixture was stirred at room temperature for 3 hours. After the reaction mixture was washed with water, the concentrated residue was purified by means of silica gel chromatography to obtain 5.71 g of oily substance, which was crystallized from ethyl acetate-hexane to afford 4.44 g of the title compound, m.p. 203°-206° C. (decomposition). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | With sulfuric acid; acetic acid at 20℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45 g | In water at -0.16 - 74.84℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | In water at 50℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | In water at 50℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With [2,2]bipyridinyl; oxygen; copper diacetate; sodium carbonate In 1,2-dichloro-ethane at 70℃; for 2h; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: N-(4-aminobutyl)acetamide; disodium adenosine-5' triphosphate With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide In water for 2h; Stage #2: triethylamine In water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane at 4 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With HATU | 2-Cyclopropyl-oxazole-4-carboxylic acid [5-(4- acetylamino-butylcarbamoyl)-2-(4-o-tolyl-piperazin-1-yl)-phenyl]-amide was prepared from N- (4-amino-butyl)-acetamide and 3-[(2-cyclopropyl-oxazole-4-carbonyl)-amino]-4-(4-o-tolyl- piperazin-1-yl)-benzoic acid obtained from the LiOH mediated hydrolysis of 3-[(2-cyclopropyl- oxazole-4-carbonyl)-amino]-4-(4-o-tolyl-piperazin-1-yl)-benzoic acid methyl ester followed by HATU amide coupling using the desired amine.LCMS (ESI) 559 (M+H); 1H NMR (400 MHz, DICHLOROMETHANE-cfe) δ ppm 1.07 - 1.18 (m, 4H) 1.53 - 1.70 (m, 4H) 2.00 (s, 3H) 2.05 - 2.15 (m, 1 H) 2.37 (s, 3H) 3.09 - 3.24 (m, 8H) 3.30 (q, 6.36 Hz, 2H) 3.43 - 3.51 (m, 2H) 6.22 - 6.47 (m, 1H) 6.68 (brs, 1H) 6.97 - 7.35 (m, 5H) 7.61 (dd, J=8.22, 2.07 Hz, 1H) 8.12 (s, 1H) 8.82 (d, .1=2.05 Hz, 1H) 9.94 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In butan-1-ol at 130℃; for 18h; | 303 Example 303N-(4-[2-Amino-6-(2,3-dichlorophenyl)pyrimidin-4-yl]amino}butyl)acetamide. Example 303N-(4-[2-Amino-6-(2,3-dichlorophenyl)pyrimidin-4-yl]amino}butyl)acetamide.A solution of 4-chloro-6-(2,3-dichlorophenyl)pyrimidin-2-amine (25 mg; 0.1 mmol)in n-BuOH (1.0 ml) was heated at 130°C with N-(4-aminobutyl)acetamide (1 eq.)and triethylamine (1 eq). After 18 h the reaction was halted and evaporated. Theresidue was purified by preparative HPLC. LCMS [M+H] 368. | |
With triethylamine In butan-1-ol at 130℃; for 18h; | 303 Example 303 N-(4-[2-Amino-6-(2,3-dichlorophenyl)pyrimidin-4-yl]amino}butyl)acetamide. Example 303 N-(4-[2-Amino-6-(2,3-dichlorophenyl)pyrimidin-4-yl]amino}butyl)acetamide. A solution of 4-chloro-6-(2,3-dichlorophenyl)pyrimidin-2-amine (25 mg; 0.1 mmol) in n-BuOH (1.0 ml) was heated at 130°C with N-(4-aminobutyl)acetamide (1 equiv.) and triethylamine (1 eq). After 18 h the reaction was halted and evaporated. The residue was purified by preparative HPLC. LCMS [M+H]+ 368. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | Stage #1: (2-((butyryloxy)methyl)thio)benzoic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 23℃; for 1h; Inert atmosphere; Stage #2: N-(4-aminobutyl)acetamide With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 23℃; for 12h; Inert atmosphere; | 4.5.7 General procedure G for the synthesis of mercaptobenzamides of general structure 13 General procedure: Chloromethyl butyrate (1.00 equiv) and N,N-di-iso-propylethylamine (1.20 equiv) were sequentially added to a solution of thiosalicylic acid (1 equiv) in N,N-dimethylformamide (0.20M) and the resulting mixture was stirred at 23°C for 12h. 1,1′-Carbonyldiimidazole (1.00 equiv) was added to the reaction mixture, and the resulting mixture was stirred at 23°C for 1h. A solution of amine (specified below; 1.00 equiv) in N,N-dimethylformamide (4.0mL) and N,N-di-iso-propylethylamine (2.30 equiv) were sequentially added to the reaction mixture, and the resulting mixture was stirred at 23°C for 12h. The product mixture was concentrated, and the residue obtained was diluted with ethyl acetate (120mL). The diluted product mixture was transferred to a separatory funnel and sequentially washed with saturated aqueous sodium bicarbonate solution (1×50mL), water (1×50mL), and saturated aqueous sodium chloride solution (1×50mL). The organic layer was dried over sodium sulfate. The dried solution was filtered and the filtrate was concentrated. The residue thus obtained was purified by flash-column chromatography (as noted) to provide the mercaptobenzamide of general structure 13. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | In ethanol at 20℃; for 18h; | 1 4-(2,3-Bis(tert-butyloxycarbonyl)guanidino)butylacetamide J-4: Commercially available N-acetylputrescine 14 (1.30 g, 1.00 mL, 9.99 mmol, 2.00 equiv) and 1,3-bis(tert- butoxycarbonyl)-2-methyl-2-thiopseudourea 11 (1.45 g, 4.99 mmol, 1.00 equiv) were dissolved in ethanol (95%, 50 mL). The homogeneous solution was stirred overnight (~18 hours) at rt. TLC indicated a complete consumption of starting material (5:4:1 EtOAc/hexanes/MeOH). The reaction mixture was concentrated to furnish a clear oil that was purified by silica gel column chromatography with an isocratic mixture of 5:4:1 EtOAc/hexanes/MeOH to afford 1.01 g (55%) of J-4 as a colorless solid. Mp 122.5-124.5. Anal. Calc’d for C15H23N4O5: C, 54,82; H, 8.66; N, 15.04. Found: C, 55.08; H, 8.55; N, 15.19.1H NMR (400 MHz, MeOH-d4) d 3.37 (t, J = 6.8 Hz, 2H), 3.20 (t, J = 6.6 Hz, 2H), 1.93 (s, 3H), 1.67- 1.54 (m, 4H), 1.53 (s, 9H), 1.47 (s, 9H);13C NMR (100 MHz, MeOH-d4) d 173.2, 164.5, 157.6, 154.2, 84.4, 80.3, 41.4, 40.1, 28.6, 28.2, 27.6, 27.5, 22.6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | In ethanol at 20℃; for 12h; | 1 4-(2,3-Bis(ethoxycarbonyl)guanidino)butylacetamide J-3. To a solution of 13 (2.00 g, 8.54 mmol) in abs. ethanol (15 mL) was added a solution of commercially available N- acetylputrescine 14, CAS Reg. No.18233-70-0 (1.2 g, 9.2 mmol) in abs. ethanol (10 mL). After the reaction was stirred overnight at rt, the solvent was removed under reduced pressure. Addition of chloroform and evaporation was repeated twice to yield 3.4 g of a viscous oil, which on triturating with hexanes:Et2O (9:1) produced white solids that were separated and washed with hexanes:Et2O (9:1) and dried under vacuum to yield 1.8 g (67%) of J-3 as a colorless solid. Mp 95- 97 °C.1H NMR (400 MHz, CDCl3) d 11.70 (s, 1H), 8.36 (t, J = 5.7 Hz, 1H), 6.05 (s, 1H), 4.22 (q, J = 7.1 Hz, 2H), 4.14 (q, J = 7.1 Hz, 2H), 3.44 (q, J = 6.6 Hz, 2H), 3.29 (q, J = 6.4 Hz, 2H), 1.98 (s, 3H), 1.63 (p, J = 7.0 Hz, 2H), 1.55 (p, J = 7.2 Hz, 2H), 1.30 (td, J = 7.1, 2.6 Hz, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | In ethanol at 20℃; for 18h; | 1 4-(2-(ethoxycarbonyl)guanidino)butylacetamide J-6: Commercially available 16 (0.809 g, 4.99 mmol, 1.00 equiv) and N-acetylputrescine 14 (1.30 g, 1.00 mL, 9.99 mmol, 2.00 equiv) were dissolved in ethanol (95%, 50 mL). The homogeneous solution was stirred overnight (about 18 hours) at rt. TLC indicated a complete consumption of starting material (5:4:1 EtOAc/hexanes/MeOH). The reaction mixture was concentrated to a clear oil which was purified by silica gel column chromatography with an isocratic mixture of 5:4:1EtOAc/hexanes/MeOH. Concentration of the desired fractions afforded 0.56 g (46%) of J-6 as a cream colored solid. Mp 118-120 °C.1H NMR (400 MHz, MeOH-d4) d 3.97 (q, J = 7.1 Hz, 2H), 3.10 (dt, J = 9.9, 6.3 Hz, 4H), 1.83 (s, 3H), 1.51- 1.41 (m, 4H), 1.15 (t, J = 7.1 Hz, 3H).13C NMR (100 MHz, MeOH-d4) d 173.33, 61.66, 41.63, 40.08, 39.93, 28.20, 27.65, 27.54, 22.54, 14.94. MS (LCMS): 245 (M+1)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | In dichloromethane at -78 - 20℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethanolamine; ethylenediaminetetraacetic acid; carnitine acetyltransferase; arylamine N-acetyltransferase 2*4, wild-type allele; acetylcarnitine; diothiothreitol In water at 37℃; for 18h; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium cyanoborohydride; acetic acid / methanol / 24 h / 20 °C / Inert atmosphere 2: acetic acid; palladium 10% on activated carbon; hydrogen / water / 4 h / 20 °C 3: arylamine N-acetyltransferase 2*4, wild-type allele; triethanolamine; acetylcarnitine; ethylenediaminetetraacetic acid; diothiothreitol; carnitine acetyltransferase / water / 18 h / 37 °C / pH 7.5 / Enzymatic reaction |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium cyanoborohydride; acetic acid / methanol / 24 h / 20 °C / Inert atmosphere 2: acetic acid; palladium 10% on activated carbon; hydrogen / water / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With sodium cyanoborohydride; acetic acid In methanol at 20℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With palladium diacetate; Cs2CO3; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 80℃; for 12h; Inert atmosphere; | 103.1 Step 1 : N-[4-[[3-cyclopropyl-4-(3-methyl-4-methylsulfonyl-phenyl)-l-tetrahydropyran-2-yl- pyrazolo[4,3-c]pyridin-7-yl]amino]butyl]acetamide To a mixture of 7-bromo-3-cyclopropyl-4-(3-methyl-4-methylsulfonyl-phenyl)-l- tetrahydropyran-2-yl-pyrazolo[4,3-c]pyridine (Example 99, step 1) (80 mg, 0.2 mmol) in 1,4- dioxane (2 mL) was added cesium carbonate (266 mg, 0.8 mmol), N-(4-aminobutyl)acetamide (106 mg, 0.8 mmol), xantphos (11 mg, 0.02 mmol) and Pd(OAc)2 (4 mg, 0.02 mmol) was stirred at 80°C for 12 h under a nitrogen atmosphere. The reaction mixture was filtered and concentrated. Purification by reversed phase preparative HPLC afforded the title compound (60 mg, 68%) as a yellow solid. ([M+H]+ 540.1) |