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[ CAS No. 1943-83-5 ] {[proInfo.proName]}

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Chemical Structure| 1943-83-5
Chemical Structure| 1943-83-5
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Product Details of [ 1943-83-5 ]

CAS No. :1943-83-5 MDL No. :MFCD00002043
Formula : C3H4ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :BCMYXYHEMGPZJN-UHFFFAOYSA-N
M.W : 105.52 Pubchem ID :16035
Synonyms :

Safety of [ 1943-83-5 ]

Signal Word:Danger Class:6.1,3
Precautionary Statements:P264-P210-P240-P241-P242-P243-P285-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P331-P310-P330-P370+P378-P363-P403+P233-P405-P501 UN#:3080
Hazard Statements:H226-H314-H334-H301+H311+H331 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1943-83-5 ]

* 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 [ 1943-83-5 ]

[ 1943-83-5 ] Synthesis Path-Downstream   1~101

  • 1
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  • [ 1709-59-7 ]
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  • 15
  • [ 6789-94-2 ]
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  • 17
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  • 18
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  • [ 35212-85-2 ]
  • [ 152032-94-5 ]
  • 19
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  • [ 30453-21-5 ]
  • 3,3'-bis<N-(2-chloroethyl)carbamoyl>propyl disulfide [ No CAS ]
  • 20
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  • [ 40137-22-2 ]
  • [ 70189-82-1 ]
  • 21
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  • [ 20637-09-6 ]
  • [ 113849-33-5 ]
  • 22
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  • [ 49705-98-8 ]
  • (2S,3R)-2-[3-(2-Chloro-ethyl)-ureido]-3-hydroxy-butyramide [ No CAS ]
  • 23
  • [ 1943-83-5 ]
  • [ 4985-46-0 ]
  • (S)-2-[3-(2-Chloro-ethyl)-ureido]-3-(4-hydroxy-phenyl)-propionamide [ No CAS ]
  • 25
  • [ 1943-83-5 ]
  • [ 1450-94-8 ]
  • 1-(1-methyl-imidazolyl)-2-imidazolidinone hydrochloride [ No CAS ]
  • 26
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  • [ 1205-72-7 ]
  • [ 74045-93-5 ]
  • 27
  • [ 1943-83-5 ]
  • [ 65414-74-6 ]
  • (S)-2-[3-(2-Chloro-ethyl)-ureido]-3-hydroxy-propionamide [ No CAS ]
  • 28
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  • [ 42105-26-0 ]
  • [ 142238-03-7 ]
  • 29
  • [ 1943-83-5 ]
  • [ 3014-80-0 ]
  • (S)-2-[3-(2-Chloro-ethyl)-ureido]-3-methyl-butyramide [ No CAS ]
  • 30
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  • [ 82437-64-7 ]
  • [ 126080-14-6 ]
  • 32
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  • [ 81528-48-5 ]
  • [ 118252-33-8 ]
  • 34
  • [ 1943-83-5 ]
  • [ 40137-24-4 ]
  • 1-(2-Chloro-ethyl)-3-(2,2-dimethyl-[1,3]dioxan-5-yl)-urea [ No CAS ]
  • 35
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  • [ 76575-71-8 ]
  • [ 118235-74-8 ]
  • 37
  • [ 1943-83-5 ]
  • [ 2696-84-6 ]
  • 1-(2-Chloro-ethyl)-3-(4-propyl-phenyl)-urea [ No CAS ]
  • 38
  • [ 1943-83-5 ]
  • [ 104-42-7 ]
  • 4-dodecyl-1-[3-(2-chloroethyl)ureido]benzene [ No CAS ]
  • 39
  • [ 1943-83-5 ]
  • [ 30273-11-1 ]
  • 4-sec-butyl-1-[3-(2-chloroethyl)ureido]benzene [ No CAS ]
  • 40
  • [ 1943-83-5 ]
  • [ 37529-30-9 ]
  • 4-decyl-1-[3-(2-chloroethyl)ureido]benzene [ No CAS ]
  • 42
  • [ 1943-83-5 ]
  • [ 5266-85-3 ]
  • 1-(2-Chloro-ethyl)-3-(2-isopropyl-6-methyl-phenyl)-urea [ No CAS ]
  • 44
  • [ 1943-83-5 ]
  • [ 68208-18-4 ]
  • 3-[3N'-(2-chloroethyl)ureido]-3-(4-methylphenyl)propionic acid [ No CAS ]
  • 45
  • [ 1943-83-5 ]
  • [ 2924-16-5 ]
  • N-(3-fluorophenyl)-N'-[(2-chloroethyl)amino]carbonyl}hydrazine [ No CAS ]
  • 46
  • [ 1943-83-5 ]
  • [ 5193-03-3 ]
  • C8H10Cl2N4O [ No CAS ]
  • 48
  • [ 1943-83-5 ]
  • [ 1134-47-0 ]
  • [ 213407-00-2 ]
  • 49
  • [ 1943-83-5 ]
  • [ 3184-13-2 ]
  • (S)-2-Amino-5-[3-(2-chloro-ethyl)-ureido]-pentanoic acid [ No CAS ]
  • 50
  • [ 1943-83-5 ]
  • [ 1482-98-0 ]
  • (S)-2-Amino-4-[3-(2-chloro-ethyl)-ureido]-butyric acid [ No CAS ]
  • 51
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  • [ 10045-45-1 ]
  • [ 240143-52-6 ]
  • 52
  • [ 26456-59-7 ]
  • [ 1943-83-5 ]
  • carbamic acid, (2-chloroethyl)-5-pyrimidine ester [ No CAS ]
  • 53
  • [ 1943-83-5 ]
  • [ 14227-17-9 ]
  • 1-(2',4',6'-trimethoxyphenyl)-3-(2'-chloroethyl)urea [ No CAS ]
  • 54
  • [ 1943-83-5 ]
  • [ 31891-06-2 ]
  • [ 181490-38-0 ]
  • 2-{3-[2-((3aR,9bR)-6-Methoxy-1,3,3a,4,5,9b-hexahydro-benzo[e]isoindol-2-yl)-ethyl]-ureido}-thiophene-3-carboxylic acid ethyl ester [ No CAS ]
  • 55
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  • [ 252932-48-2 ]
  • [ 850145-19-6 ]
  • 56
  • [ 1943-83-5 ]
  • [ 52273-77-5 ]
  • 1-(2-chloro-ethyl)-3-[3-(2-hydroxy-ethyl)-phenyl]-urea [ No CAS ]
  • 57
  • [ 1943-83-5 ]
  • [ 34761-09-6 ]
  • [ 167225-15-2 ]
  • 58
  • [ 1943-83-5 ]
  • [ 6330-25-2 ]
  • 2-cyano-<i>N</i>-methyl-2-oxazolidin-2-ylidene-acetamide [ No CAS ]
  • 59
  • [ 1943-83-5 ]
  • [ 6330-25-2 ]
  • 6-(2-chloro-ethyl)-5,7-dioxo-1,2,3,5,6,7-hexahydro-imidazo[1,2-<i>c</i>]pyrimidine-8-carboxylic acid methylamide [ No CAS ]
  • 60
  • [ 1943-83-5 ]
  • [ 32202-61-2 ]
  • C12H15N2OCl [ No CAS ]
  • 61
  • [ 1943-83-5 ]
  • [ 153-78-6 ]
  • 2-[3-(2-chloroethyl)ureido]fluorene [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% In diethyl ether; EXAMPLE V Preparation of 2-[3-(2-chloroethyl)ureido]fluorene To a solution of 2 g of <strong>[153-78-6]2-aminofluorene</strong> in 125 mL of anhydrous ethyl ether is added dropwise 1.25 g of 2-chloroethyl isocyanate. This solution is stirred for 16 h at room temperature, cooled at -20 C., and filtered. A white solid separated and was recrystallized from ethanol (white flakes), yield 40%, mp 206-208 C., IR (KBr pellet): 3300 (NH), 1730 (C=O, ester), and 1640 cm-1 (C=O, ureido); 1 H NMR (DMSO-d6: CDCl3): 8.08 ppm, 7.44 ppm, 7.35 ppm, 7.3 ppm, 7.27 ppm, 7.25 ppm, 7.16 ppm, 7.13 ppm, 7.02 ppm, 6.97 ppm, 6.96 ppm, 6.94 ppm, 6.93 ppm, 6.9 ppm, 6.87 ppm, 6.8 ppm, 3.5 ppm, 3.36 ppm, 3.33 ppm, 3.3 ppm, 3.25 ppm, 3.23 ppm, 3.2 ppm, 2.85 ppm.
  • 62
  • [ 1943-83-5 ]
  • [ 950-58-3 ]
  • N-[3,5-bis-(1,1-dimethylethyl)-4-hydroxyphenyl]-N'-(2-chloroethyl)urea [ No CAS ]
  • 63
  • [ 154590-35-9 ]
  • [ 1943-83-5 ]
  • [ 1364550-23-1 ]
YieldReaction ConditionsOperation in experiment
In DMF (N,N-dimethyl-formamide); at 60℃; for 18h; Step 1: Combine the product of Preparation 13, Step 3 (2.2 g, 6.7 mmol) and 2-chloroethyl isocyanate (0.64 ml, 7.4 mmol) in DMF (30 ml). Heat at 60 C. 18 h, allow to cool and partition with CH2Cl2 and water. Dry (MgSO4) and concentrate to obtain the crude urea as a yellow solid.
In DMF (N,N-dimethyl-formamide); at 60℃; for 18h; Combine the product of Preparation 17, Step 3 (2.2 g, 6.7 mmol) and 2-chloroethyl isocyanate (0.64 ml, 7.4 mmol) in DMF (30 ml). Heat at 60 C. 18 h, allow to cool and partition with CH2Cl2 and water. Dry (MgSO4) and concentrate to obtain the crude urea as a yellow solid.
  • 64
  • [ 1943-83-5 ]
  • [ 578-68-7 ]
  • 1-(2-chloroethyl)-3-quinolin-4-yl-urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; for 18h; To a solution of 4-AMINOQUINOLINE (3.46 g, 24 MMOL) in dry THF is added CHLOROETHYLISOCYANATE (3.1 mL, 36 MMOL). The reaction mixture is stirred for 18 h. MEOH (10 mL) is added, and stirring is continued for an additional hour. The reaction mixture is evaporated, and partitioned between DCM and aqueous 5% citric acid (150 mL). The aqueous layer is carefully adjusted to pH 9 with solid NAHCO3. The precipitate is filtered, washed with H20 (5 x 20 mL) and Et20 (2 x 20 mL), and dried in vacuo at 45 C to provide the title compound
  • 65
  • [ 1943-83-5 ]
  • [ 35472-56-1 ]
  • 3-(2-chloroethyl)-1-methyl-2,4(1H,3H)-quinazolinedione [ No CAS ]
YieldReaction ConditionsOperation in experiment
In toluene; EXAMPLE 26 3-[2-(cis-6-Methoxy-2,3,3a,4,5,9b-hexahydro-[1H]-benz[e]isoindol-1-yl)ethyl]-1-methyl-quinazoline-2,4(1H,3H)-dione hydrochloride N-Methyl-2-carboethoxyaniline (5.0 g, 28 mmol) was treated with 2-chloroethylisocyanate (2.86 mL, 28 mmol) at reflux in toluene for 18 hours. The reaction was cooled to 25 C., and the crystalline product was collected by filtration to yield the intermediate 1-methyl-3-(2-chloroethyl)-quinazoline-2-4-dione.
In toluene; EXAMPLE 26 3-[2-(cis-6-Methoxy-2,3,3a,4,5,9b-hexahydro-[1H]-benz[e]isoindol-1-yl)ethyl]-1-methyl-quinazoline-2,4(1H,3H)-dione hydrochloride N-Methyl-2-carboethoxyaniline (5.0 g, 28 mmol) was treated with 2-chloroethylisocyanate (2.86 mL, 28 mmol) at reflux in toluene for 18 hours. The reaction was cooled to 25 C., and the crystalline product was collected by filtration to yield the intermediate 1-methyl-3-(2-chloroethyl)quinazoline-2-4dione.
  • 66
  • [ 1943-83-5 ]
  • [ 43088-42-2 ]
  • 3-[2-(cis-6-Methoxy-2,3,3a,4,5,9b-hexahydro-[1H]-benz[e]isoindol-1-yl)ethyl]-5-methylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione hydrochloride [ No CAS ]
  • [ 181490-38-0 ]
YieldReaction ConditionsOperation in experiment
41% EXAMPLE 4 3-[2-(cis-6-Methoxy-2,3,3a,4,5,9b-hexahydro-[1H]-benz[e]isoindol-1-yl)ethyl]-5-methylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione hydrochloride 2-Amino-3-carboethoxy-4-methylthiophene was treated with 2-chloroethylisocyanate by the procedures described in Example 3. The resulting urea (0.35 g, 1.2 mmol) and cis-6-methoxy-2,3,3a,4,5,9b-hexahydro[1H]-benz[e]isoindole (0.23 g, 1.1 mmol) were treated by the procedures described in Example 3 to afford the title compound (0.11 g, 41percent) was obtained as a white solid. m.p. 179°-181° C. 1 H NMR (500 MHz, DMSO-d6) delta 1.40-1.48(m, 1H), 1.60-1.67 (m, 1H), 2.12-2.19 (m, 1H), 2.24 (dd, 1H), 2.34 (s, 3H), 2.41-2.49 (m, 2H), 2.52-2.63 (m, 3H), 3.13 (t, 1H), 3.23-3.30 (m, 2H), 3.75 (s, 3H), 3.94 (t, 2H), 6.64 (s, 1H), 6.72 (d, 1H), 6.74 (d, 1H), 7.08 (t, 1H). MS (DCI/NH3) m/e 412 (M+H)+. Anal calcd for C22 H25 N3 O3 S.HCl.2 H2 O: C, 54.59; H, 6.25; N, 8.68. Found: C, 54.30; H, 5.64; N, 8.47.
41% EXAMPLE 4 3-[2-(cis-6-Methoxy-2,3,3a,4,5,9b-hexahydro-[1H]-benz[e]isoindol-1-yl)ethyl]-5-methylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione hydrochloride 2-Amino-3-carboethoxy-4methylthiophene was treated with 2-chloroethyl-isocyanate by the procedures described in Example 3. The resulting urea (0.35 g, 1.2 mmol) and cis-6-methoxy-2,3,3a,4,5,9b-hexahydro[1H]-benz[e]isoindole (0.23 g, 1.1 mmol) were treated by the procedures described in Example 3 to afford the title compound (0.11 g, 41percent) was obtained as a white solid. m.p. 179°-181° C. 1 H NMR (500 MHz, DMSO-d6) delta 1.40-1.48 (m, 1H), 1.60-1.67 (m, 1H), 2.12-2.19 (m, 1H), 2.24 (dd, 1H), 2.34 (s, 3H), 2.41-2.49 (m, 2H), 2.52-2.63 (m, 3H), 3.13 (t, 1H), 3.23-3.30 (m, 2H), 3.75 (s, 3H), 3.94 (t, 2H), 6.64 (s, 1H), 6.72 (d, 1H), 6.74 (d, 1H), 7.08 (t, 1H). MS (DCI/NH3) m/e 412 (M+H)+. Anal calcd for C22 H25 N3 O3 S*HCl*2 H2 O: C, 54.59; H, 6.25; N, 8.68. Found: C, 54.30; H, 5.64; N, 8.47.
  • 67
  • [ 1943-83-5 ]
  • [ 68-94-0 ]
  • [ 104789-47-1 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In N-methyl-acetamide; EXAMPLE 2 6-[N-(2-Chloroethyl)carbamoyl]oxypurine (Ib) To a suspension of hypoxanthine (6.8 g, 50 mmoles) in dimethylformamide (200 ml) there is added triethylamine (5.05 g, 50 mmoles) and then at 15 to 20 C., 2-chloroethylisocyanate (5.8 g, 55 mmoles is dripped in. The reaction mixture is stirred at this temperature until dissolution of the solid (approx. for 2 hours), thereafter poured into an ice-water mixture (750 ml), the precipitate of the title product is separated by suction, washed with acetone and dried at room temperature. The yield is 8.2 g (67.8%) of compound Ib, m.p. 320-240 C. (with decomposition), UV absorption spectrum (in dimethylsulfoxide), lambda max 275 nm (log ·3.76).
  • 68
  • [ 1943-83-5 ]
  • [ 54326-16-8 ]
  • [ 86673-37-2 ]
YieldReaction ConditionsOperation in experiment
40% In N,N-dimethyl-formamide; EXAMPLE 6 1-(2-Chloroethyl)carbamoyl-<strong>[54326-16-8]5-chloropyrimidin-2-one</strong> was prepared from <strong>[54326-16-8]5-chloropyrimidin-2-one</strong> and 2-chloroethylisocyanate in dimethyl formamide as described above; yield 40%. 1 H NMR (DMSO-d6): delta3.6 (CH2 CH2, broad m), 8.41 (2H-4,6), 9.5 (NH).
  • 69
  • [ 1943-83-5 ]
  • [ 68-94-0 ]
  • 6-[N-(2-Chloroethyl)-carbamoyl] oxypurine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In N-methyl-acetamide; Example 2 6-[N-(2-Chloroethyl) carbamoyl] oxypurine (Ib). To a suspension of hypoxanthine (6.8 g, 50 mmoles) in dimethylformamide (200 ml) there is added triethylamine (5.05 g, 50 mmoles) and then, at 15 - 20C, 2-chloroethylisocyanate (5.8 g, 55 mmoles) is dropped in. The reaction mixture is stirred at this temperature until dissolution of the solid (approx for 2 hours), thereafter poured into an ice-water mixture (750 ml), the precipitate of the title product is separated by suction, washed with acetone and dried at room temperature. The yield is 8.2 g (67.8%) of compound Ib, mp 320 - 340C (with decomposition), UV absorption spectrum (in dimethylsulfoxide), lambda max275 nm (logepsilon 3.76).
  • 70
  • [ 120278-07-1 ]
  • [ 1943-83-5 ]
  • [ 72349-01-0 ]
YieldReaction ConditionsOperation in experiment
Method R Preparation of 1-piperidin-4-ylimidazolidin-2-one Step 1: Preparation of benzyl 4-(2-oxoimidazolidin-1-yl)piperidine-1-carboxylate; 2-Chloroethylisocyanate (2.23 g) was added to a solution of <strong>[120278-07-1]benzyl 4-aminopiperidine-1-carboxylate</strong> (5 g) (CAS 120278-07-1) in THF (100 ml) and the mixture was stirred at room temperature for 1 hour. Lithium bis(trimethylsilyl)amide (21 ml of 1M solution in THF) was added and stirring was continued for 16 hours. The clear solution was evaporated to dryness and the residue was dissolved in dichloromethane (50 ml) and the solution was washed with 2M HCl (2×50 ml) and dried. The residue obtained on evaporation of the solvent was purified by chromatography on silica eluting with a solvent gradient of 30% ethyl acetate/isohexane-ethyl acetate, yield 3.2 g.
  • 71
  • [ 1943-83-5 ]
  • [ 129743-47-1 ]
  • [ 803729-91-1 ]
  • 72
  • [ 1943-83-5 ]
  • [ 52913-11-8 ]
  • [ 803730-10-1 ]
  • 73
  • [ 1943-83-5 ]
  • [ 92050-16-3 ]
  • [ 1063656-13-2 ]
  • 74
  • [ 1943-83-5 ]
  • [ 39905-48-1 ]
  • [ 1043931-98-1 ]
  • 75
  • [ 1943-83-5 ]
  • [ 150683-30-0 ]
  • [ 1094837-55-4 ]
YieldReaction ConditionsOperation in experiment
dmap; In toluene; at 80℃; for 24h; <strong>[150683-30-0]Tolvaptan</strong> (1.0 g, 2.2 mmol) was suspended in toluene (7 ml). 2-Chloroethyl isocyanate (0.28 ml, 3.3 mmol) and 4- dimethylaminopyridine (DMAP) (27 mg, 0.22 mmol) were added thereto, and the mixture was stirred at 800C for 24 hours. After cooling to room temperature, the insoluble materials were filtered off and washed with ethyl acetate. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (n-hexane : ethyl acetate = 54 : 46 ? 33 : 67 ). The purified product was concentrated under reduced pressure to obtain 1.0 g of {7-chloro-l-[2-methyl-4-(2- methyl-benzoylamino) -benzoyl] -2 , 3 , 4 , 5-tetrahydro-IH- benzo[b]azepin-5-yl} (2-chloroethyl)carbamate as white amorphous solid. 1H-NMR (DMSO-d6, 100 C)dppm : 1.6-2.2 (4H, m) , 2.36 (6H, s), 2.6-4.3 (2H, m) , 3.42 (2H, t. <n="53"/>J=6 . 0 Hz ) , 3 . 64 ( 2H , dd, J=6 . 0 , 12 . 1 Hz ) , 5 . 8- 5 .9 ( 3H, m) , 6 . 7 - 7 . 5 ( 1OH , m) , 7 . 56 ( IH , s ) , 9 .8 ( IH , br) .
  • 76
  • [ 1943-83-5 ]
  • [ 71569-15-8 ]
  • C12H16ClN3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; at 20.0℃; for 1.5h; To 5,6,7,8-tetrahydroquinolin-8-amine (Intermediate 17) (3.0 mmol) in dichloromethane (10 mL) was added chloroethylisocyanate (3.3 mmol). The solution was stirred at room temperature for 1.5 hour. The solvent was removed under vacuum gave a crude material, which was refluxed in H2O (60 mL) for 1 hour. After cooling to room temperature, the reaction was basified with NaOH (pH 14), extracted in Ethyl acetate (3 x 50 mL). The pooled organic layers were washed with brine and dried over magnesium sulphate to give 747. (4, 5-Dihydro-oxazol-2-yl)-(5,6,7,8-tetrahydro- quinolin-8-yl)-amine, 747 as a solid.1HNMR (CDCl3, 300MHz): delta = 6.89-7.34 (m, 4H), 5.21 (s, J= 4.5 Hz, IH), 4.01- 4.07 (m, 2H), 3.34-3.39 (m, 2H), 2.82-2.96 (m, 2H), 2.59-2.67 (m, IH), 1.91-1.99 (m, IH).
  • 77
  • [ 1943-83-5 ]
  • [ 57233-86-0 ]
  • (R)-2-(1-(4-nitrophenyl))ethylaminooxazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% (R)-alphamethyl-4-nitrobenzylamine hydrochloride (645 mg, 0.32 mmole) was suspended in 5 ml tetrahydrofuran and stirred with triethylamine (330 mg) for 1 hour. 2-chloroethylisocyanate (360 mg, 95%) was added in 5 ml tetrahydrofuran with stirring and the mixture stirred for 4 hours. 6 ml of water was then added followed by 2 ml 10 molar sodium hydroxide and the mixture heated to reflux for 24 hours. The mixture was then diluted with 50 ml ethyl acetate and shaken. The aqueous phase was discarded and the organic layer washed with 5 ml water, then extracted twice with 5 ml 1 molar hydrochloric acid. The extracts were combined and basified with 10 molar sodium hydroxide. The precipitated product was extracted with 25 ml ethyl acetate, washed with water and then reduced to dryness in vacuo. The product forms pale yellow crystals on drying, mp. 112-116 C. Yield 0.62 g (83%). Proton nmr in CDCl3 shows 7.8 (4H dd, J=9 and 42 Hz), 4.8 (1Hq, J=7 Hz), 3.9 (4Hm) 1.4(3H d, J=7 Hz).
  • 78
  • [ 1943-83-5 ]
  • [ 60-19-5 ]
  • C11H15ClN2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Tyramine hydrochloride (1.04 g) was stirred in 5 ml tetrahydrofuran with triethylamine 860 mul for 16 hours, after which 2-chloroethylisocyanate (540 mul) was added and stirring continued for 24 hours. The mixture was extracted into ethyl acetate and washed with 1M hydrochloric acid (10 ml) and water, before reducing to dryness in vacuo. The residue was redissolved in tetrahydrofuran (5 ml) and water (5 ml) containing sodium sulfite (50 mg). 5 molar sodium hydroxide (2 ml) was added and the mixture heated to reflux for 5 hours. Sodium dihydrogen phosphate (1 g was then added with stirring) and the mixture reduced to dryness in vacuo. The product was isolated by extraction with chloroform (10 ml) and isopropanol (2×10 ml). The combined extracts were reduced to dryness and reconstituted in ethyl acetate containing 10% methanol. The mixture was separated by chromatography on silica gel, and eluted with mixtures of ethyl acetate and methanol. The combined eluates were reduced to dryness to give a crystalline solid (450 mg, 35%), mp. 90-96 C. Proton nmr in deuterated methanol shows, 6.7 (4H q), 4.5- 3.0 (6H m) 2.5 (2H br.tr., J=8 Hz). Chemical ionisation mass spectrum shows m/e 207 (MH+).
  • 79
  • [ 1943-83-5 ]
  • [ 1122-58-3 ]
  • [ 150683-30-0 ]
  • [ 1094837-55-4 ]
YieldReaction ConditionsOperation in experiment
In toluene; Example 28 {7-Chloro-1-[2-methyl-4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl}(2-chloroethyl)carbamate <strong>[150683-30-0]Tolvaptan</strong> (1.0 g, 2.2 mmol) was suspended in toluene (7 ml). 2-Chloroethyl isocyanate (0.28 ml, 3.3 mmol) and 4-dimethylaminopyridine (DMAP) (27 mg, 0.22 mmol) were added thereto, and the mixture was stirred at 80 C. for 24 hours. After cooling to room temperature, the insoluble materials were filtered off and washed with ethyl acetate. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (n-hexane:ethyl acetate=54:46?33:67). The purified product was concentrated under reduced pressure to obtain 1.0 g of {7-chloro-1-[2-methyl-4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl}(2-chloroethyl)carbamate as white amorphous solid. 1H-NMR (DMSO-d6, 100 C.) delta ppm: 1.6-2.2 (4H, m), 2.36 (6H, s), 2.6-4.3 (2H, m), 3.42 (2H, t, J=6.0 Hz), 3.64 (2H, dd, J=6.0, 12.1 Hz), 5.8-5.9 (3H, m), 6.7-7.5 (10H, m), 7.56 (1H, s), 9.8 (1H, br).
  • 80
  • [ 1943-83-5 ]
  • [ 773-76-2 ]
  • [ 1221161-42-7 ]
  • 81
  • [ 1943-83-5 ]
  • [ 491-80-5 ]
  • [ 1374694-38-8 ]
YieldReaction ConditionsOperation in experiment
81% With pyridine; In diethyl ether; at 0 - 20℃; General procedure: For the preparation of the esters and the carbamide esters of BCA, in a solution of BCA (100 mg, 0.35 mmol) in 20 mL ether which was cooled to 0 C, 0.8 mL of pyridine and 0.50 mL of the corresponding acylchlorides or isocyanates were added. After the completion of the reaction in room temperature, the organic solvents were evaporated and the residue was chromatographed on a silica gel column chromatography using as mobile phase a gradient CH2Cl2/MeOH mixture, to afford the relative compound.
  • 82
  • [ 1943-83-5 ]
  • [ 847171-68-0 ]
  • [ 1383607-33-7 ]
YieldReaction ConditionsOperation in experiment
45% dmap; In tetrahydrofuran; for 168.0h;Inert atmosphere; Reflux; 2-Chloroethylisocyanate (1.2 mmol) and 4-dimethylaminopyridine were added dropwise to a solution of the appropriate aniline (1 .0 mmol) in dry tetrahydrofuran (10 mL) under argon atmosphere. The reaction mixture was heated to reflux and stirred for 7 days. Afterward cooling to room temperature, the solvent was evaporated under reduced pressure and the crude compound was purified by flash chromatography. The crude product was purified by flash chromatography (silica gel, methylene chloride to methylene chloride/ethyl acetate (90:10)) and was crystallized with methylene chloride and filtered. Yield: 45%; White solid; mp: 164-165 C; IR delta: 3267 (NH), 1642 (CO) cm"1; 1H NMR (DMSO-d6): delta 9.58 (s, 1 H, NH), 9.06 (s, 1 H, NH), 7.94 (s, 1 H, Ar), 7.62-7.01 (m, 7H, Ar), 6.51 (brs, 1 H, NH), 3.71-3.68 (m, 2H, CH2), 3.48-3.45 (m, 2H, CH2), 2.05 (s, 3H, CH3); 13C NMR (DMSO-d6): delta 154.8, 141 .3, 141 .0, 134.9, 134.3, 130.7, 129.5, 126.5, 126.4, 126.3, 121.3,119.2, 1 15.4, 44.3, 41.3, 17.7; MS (APS I -) m/z found 366.0; C16H17CIN303S (M" - H) requires 366.1.
  • 83
  • [ 1943-83-5 ]
  • [ 39959-67-6 ]
  • [ 1067671-84-4 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 20℃; for 15h; Step 1 3,2 g (20.6mmol) 1-(2-chlorophenyl)ethaneamine [CAS 39959-67-6] and 52.3 g (22.6 mmol) triethylamine were given into 20 ml dichloromethane and afterwards 2.4 g (22.6 mmol) 2-chloroethylisocyanat werde added dropwise. The mixture was allowed to react 15 hours at 20C. The volatile components were evaporated to give 1-(2-chloroethyl)-3-[1-(2-chlorophenyl)ethyl]urea (log p = 2.3) that was used in step 2 without further purification
  • 84
  • [ 1943-83-5 ]
  • [ 360-97-4 ]
  • [ 85622-95-3 ]
YieldReaction ConditionsOperation in experiment
Briefly, <strong>[360-97-4]5-aminoimidazole-4-carboxamide</strong> was treated with NaNO2 and the resulting product reacted with 2-chloroethylisocyanate in ethyl acetate to provide MTZ.
  • 85
  • [ 1943-83-5 ]
  • [ 62-53-3 ]
  • [ 1848-69-7 ]
YieldReaction ConditionsOperation in experiment
26% A solution 2-chloroethyl isocyanate (1.05 g, 10 mmol) in THF (50 mL) was added dropwise to a stirring solution of phenylamine (0.93 g, 10 mmol) in THF (20 mL) at -20 C. The solution was brought to room temperature overnight. The resulting reaction mixture was treated with NaH (0.24 g, 10 mmol) under an inert atmosphere and stirred at room temperature overnight. The mixture was treated with saturated NH4CI (100 mL) and EtOAc (200 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (3 x 50 mL). The combined organic fractions were dried over Na2S04 and concentrated under vacuum to form a colorless suspension in EtOAc. The reaction mixture was filtered and the resulting solid was dried to form the desired product. Yield (0.42 g, 26%). 1 H NMR (CDCI3, 300 MHz, 298 K): 5 7.58 (d, 2H, JH.H =8.2 Hz, m-CeH5), 7.38-7.29 (m, 2H, o-C6H5), 7.05 (t, 2H, JH-H =7.2 Hz, p-C6H5), 4.00-3.84 (m, 2H, PhNCH2), 3.65-3.48 (m, 2H, HNCW2) ppm. "C NMR (CDCI3, 75 MHz, 298 K): delta 160.27 (OO), 140.18 (C6H5), 128.92 (C6H6), 122.83 (C6H5), 1 18.09 (C6H5), 45.49 (PhNCH2), 37.70 (HNCH2) ppm. HRMS (ESI): m/z calcd for C9H10N2ONa [M+Na+]: 185.0691. Found: 185.0691. Figure 24 is a 1H NMR spectrum (300 MHz, CDCI3, 298 K) of 1-phenylimidazolidin-2-one (PhLH). Figure 25 is a 1H NMR spectrum (75 MHz, CDCI3, 298 K) of 1- phenylimidazolidin-2-one (PhLH).
26% A solution 2-chloroethyl isocyanate (1.05 g, 10 mmol) in THF (50 mL) was added dropwise to a stirring solution of phenylamine (0.93 g, 10 mmol) in -20 C. The solution was brought to room temperature overnight. The resulting reaction mixture was treated with NaH (0.24 g, 10 mmol) under an inert atmosphere and stirred at room temperature overnight. The mixture was treated with saturated NH4CI (100 mL) and EtOAc (200 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (3 x 50 mL). The combined organic fractions were dried over Na2S04 and concentrated under vacuum to form a colorless suspension in EtOAc. The reaction mixture was filtered and the resulting solid was dried to form the desired product. Yield (0.42 g, 26%). 1H NMR (CDCI3, 300 MHz, 298 K): 67.58 (d, 2H, JH-H =8.2 Hz, m-CBH5), 7.38-7.29 (m, 2H, o-C6H6), 7.05 (t, 2H, JH-H =7.2 Hz, p-C6H5), 4.00-3.84 (m, 2H, PhNCH2), 3.65-3.48 (m, 2H, HNC H2) ppm. 13C NMR (CDCI3, 75 MHz, 298 K): 6 160.27 (C=0), 140.18 (C6H5), 128.92 (C6H5), 122.83 (C6H5), 118.09 (C6H6), 45.49 (PhNCH2), 37.70 (HNCH2) ppm. HRMS (ESI): m/z calcd for C9H10N2ONa [M+Na+]: 185.0691. Found: 185.0691. Figure 24 is a 1H NMR spectrum (300 MHz, CDCI3, 298 K) of 1-phenylimidazolidin-2-one (PhLH). Figure 25 is a 1H NMR spectrum (75 MHz, CDCI3, 298 K) of 1- phenylimidazolidin-2-one
Syntheses and characterization of compound 1 were previously reported (Fortin, S.; Wei, L; Moreau, E.; Lacroix, J.; Cote, M.-F.; Petitclerc, E.; P. Kotra, L; C.-Gaudreault, R. J. Med. Chem. 2011 , 54, 4559-4580). 2-Chloroethylisocyanate (1 .2 eq.) was added dropwise to a cold solution (ice bath) of the required aniline (1.0eq.) in dry methylene chloride (15 ml_ per g of aniline). The ice bath was then removed and the reaction mixture was stirred at room temperature for 24 h. After completion of the reaction, the solvent was evaporated under reduced pressure to give white solid, which was triturated twice in a mixture of cold hexanes/ether 10: 1 . Afterwards, sodium hydride (3 eq.) was added slowly to a cold solution of the white solid (1 eq.) in tetrahydrofuran under dry nitrogen atmosphere. The ice bath was then removed after 30 min and the reaction mixture was stirred at room temperature for 5 h. The reaction was quenched at 0 C with water and diluted with ethyl acetate. The organic layer was washed with water, brine and dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to provide compound 1 , which was used without further purification.
  • 86
  • [ 1943-83-5 ]
  • [ 51516-67-7 ]
  • [ 1381442-26-7 ]
  • 87
  • [ 1943-83-5 ]
  • [ 51516-68-8 ]
  • [ 1452871-34-9 ]
  • 88
  • [ 1943-83-5 ]
  • [ 77611-37-1 ]
  • [ 1585209-74-0 ]
YieldReaction ConditionsOperation in experiment
With pyridine; In N,N-dimethyl-formamide; for 5h; Step 1 : In a 4mL vial with magnetic stirrer was placed Boc-N-6-hydroxynorleucine (50mg, leq) and DMF (ImL). To this was added 2-chloroethyl isocyanate (17.3mg, l.Oeq) and pyridine (32.3uL, 2 eq). The vial was capped and allowed to stir for 5h. The solution was transferred to a extraction funnel, diluted with ethylacetate and lOOmM citric acid. The mixture shaken and the layers separated. The aqueous layer was extracted with ethyl acetate two additional times. The organic layers combined, washed with 5% lithium chloride, dried with sodium sulfate, filtered and concentrated. The product was identified by mass spectrometry and taken forward into the next step directly.
  • 89
  • [ 1943-83-5 ]
  • [ 675112-70-6 ]
  • 1-(4,4-difluorocyclohexyl)imidazolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% A solution of 4,4-difluorocyclohexanamine hydrochloride (0.800 g, 4.66 mmol) in THF (20 mL) was treated with Na2CO3 (0.800 g, 7.55 mmol) followed by 1-chloro-2-isocyanatoethane (0.800 g, 7.58 mmol) and stirred at RT for 2 h. The mixture was cooled to 0 C., treated with NaH (60% in mineral oil, 0.300 g, 7.50 mmol), warmed to RT and stirred for 4 h. The mixture was poured into satd. NH4Cl solution, the layers separated and the aqueous layer extracted with DCM (3*). The combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness to afford 1-(4,4-difluorocyclohexyl)imidazolidin-2-one (624 mg, 66%) as a white solid. MS (ESI) m/z: 205.1 (M+H+).
  • 90
  • [ 1943-83-5 ]
  • [ 25850-22-0 ]
  • 1-(2-chloroethyl)-3-(2,2-dimethyltetrahydro-2H-pyran-4-yl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% In tetrahydrofuran; at 0 - 20℃; Example 13 A 0 C. suspension of <strong>[25850-22-0]2,2-dimethyltetrahydro-2H-pyran-4-amine</strong> (0.806 g, 6.24 mmol) in THF (30 mL) was treated drop-wise with 2-chloroethyl isocyanate (0.585 mL, 6.86 mmol), allowed to warm to RT as the cooling bath expired and stirred overnight. The mixture was treated with additional 2-chloroethyl isocyanate (160 muL) and stirred at RT for an additional 24 hours, then concentrated to dryness, the residue dissolved in EtOAc and washed with saturated NH4Cl (1*), NaHCO3 (1*) and brine (1*), dried over MgSO4 and concentrated to dryness to afford 1-(2-chloroethyl)-3-(2,2-dimethyltetrahydro-2H-pyran-4-yl)urea (700 mg, 48%) as a yellow oil. MS (ESI) m/z: 235.1 (M+H+).
  • 91
  • [ 1943-83-5 ]
  • [ 626220-76-6 ]
  • (S)-1-(2-chloroethyl)-3-(1-methoxypropan-2-yl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With pyridine; In tetrahydrofuran; at 20℃; A mixture of <strong>[626220-76-6](R)-1-methoxypropan-2-amine hydrochloride</strong> (500 mg, 3.98 mmol) and pyridine (315 mg, 3.98 mmol) in THF (15 mL) was treated drop-wise with 2-chloroethylisocyanate (420 mg, 3.98 mmol) and stirred at RT overnight. The mixture was concentrated to dryness, partitioned between EtOAc and brine and the organic layer dried over Na2SO4 and concentrated to dryness to afford (S)-1-(2-chloroethyl)-3-(1-methoxypropan-2-yl)urea (393 mg, 50%). 1H NMR (400 MHz, DMSO-d6): delta 6.08 (s, 1H), 5.93 (d, J=8.1 Hz, 1H), 3.71 (m, 1H), 3.56-3.51 (m, 3H), 3.30-3.23 (m, 3H), 3.22 (s, 3H), 0.98 (d, J=6.7 Hz, 3H).
  • 92
  • [ 1943-83-5 ]
  • [ 111769-27-8 ]
  • (R)-1-(2-chloroethyl)-3-(tetrahydrofuran-3-yl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% A 0 C. suspension of <strong>[111769-27-8](R)-(+)-tetrahydro-3-furylamine p-toluenesulfonate salt</strong> (1.00 g, 3.86 mmol) in THF (40 mL) was treated with NaH (60% in mineral oil, 0.170 g, 4.24 mmol), stirred at 0 C. for 1.5 h, treated with 2-chloroethyl isocyanate (0.362 mL, 4.24 mmol) and stirred at RT overnight as the cooling bath expired. The mixture was treated with satd. NH4Cl and water, extracted with EtOAc (2*) and the combined organics were washed with brine (2*), dried over Na2SO4 and concentrated to dryness. The residue was treated with 1:1 EtOAc/Hex and the resulting solid collected via filtration to afford (R)-1-(2-chloroethyl)-3-(tetrahydrofuran-3-yl)urea (522 mg, 70%). MS (ESI) m/z: 193.1 (M+H+).
  • 93
  • [ 1943-83-5 ]
  • [ 110223-15-9 ]
  • 1-(3-(benzyloxy)pyrazin-2-yl)-3-(2-chloroethyl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
71.33% With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; for 15h;Reflux; 3-(3-benzyloxy)pyrazin-2-amine (100 mg, 0.50 mmol) and 2-chloroethyl isocyanate (50 muL, 0.60 mmol), DIPEA (0.26 mL, 1.50 mmol) was dissolved in tetrahydrofuran (0.25 M ) and heated under reflux for 15 hours. After completion of the reaction, the solvent was concentrated under reduced pressure, and the residue was purified by column chromatography (ethyl acetate / n-hexane = 1/2) to give the title compound 109 mg at a yield of 71.33%.
71.3% With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; for 18h;Inert atmosphere; Schlenk technique; Reflux; General procedure: 2-Chloroethyl isocyanate (0.1 mL, 1.1 mmol) was added to a solutionof the appropriate 2-amino-3-benzyloxy pyrazine derivative(0.92 mmol) in dry THF (5 mL) in the presence of DIPEA (0.5 mL,2.75 mmol). The reaction mixture was refluxed for 18 h and evaporatedafter cooling. The residue was purified by flash columnchromatography (SiO2, EA/n-Hex 1/4).
  • 94
  • [ 1943-83-5 ]
  • [ 369-35-7 ]
  • 1-(2-chloroethyl)-3-(2-fluoro-4-nitrophenyl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% In 1,2-dimethoxyethane; for 4.5h;Reflux; Example 1A 1-(2-Chloroethyl)-3-(2-fluoro-4-nitrophenyl)urea 5 ml of 2-chloroethyl isocyanate were added to 10 g (64 mmol) of <strong>[369-35-7]2-fluoro-4-nitroaniline</strong> in 44.2 ml of 1,2-dimethoxyethane. The mixture was heated under reflux for 1.5 hours, a further 2 ml of 2-chloroethyl isocyanate were added and the mixture was then heated under reflux for a further 1.5 h. Another 1.6 ml of 2-chloroethyl isocyanate were added. Thus, in total 8.79 g (83 mmol) of 2-chloroethyl isocyanate were added. After 1.5 h of heating at reflux, the mixture was cooled and filtered and the filtrate was concentrated under reduced pressure. The residue was then co-evaporated with toluene, water was then added, the mixture was extracted with ethyl acetate and the organic extract was concentrated. The residue was stirred with diethyl ether and filtered off with suction. This gave 10.16 g (61% of theory) of the title compound. LC-MS (Method 1): Rt=1.01 min; m/z=262 (M+H)+. 1H-NMR (400 MHz, DMSO-d6): delta=3.47 (m, 2H), 3.70 (m, 2H), 7.20 (m, 1H), 7.20 (t, 1H), 8.08 (dd, 1H), 8.12 (dd, 1H), 8.48 (t, 1H), 9.18 (s, 1H).
  • 95
  • [ 1943-83-5 ]
  • [ 1211533-83-3 ]
  • 1-(5-bromo-6-methoxypyridin-2-yl)-3-(2-chloroethyl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% In dichloromethane; at 0 - 20℃; for 20h;Inert atmosphere; 5-Bromo-6-methoxypyridin-2-amine (1 g, 4.93 mmol) was taken in dichloromethane (30 mL) under nitrogen atmosphere. Cooled to 0 C and added 2-chloroethyl isocyanate (2.079 g, 19.70 mmol) dropwise and the reaction mixture was stirred at RT for 20 h. Solvent was removed under reduced pressure and the residue obtained was washed with hexanes and dried under suction to give 1-(5-bromo-6- methoxypyridin-2-yl)-3-(2-chloroethyl)urea (1.12 g, 3.60 mmol, 73% yield) as an off- white solid. MS(ESI) m/z: 308.0 (M+H) ?H NMR (400 MHz, DMSO-d6) oe ppm 9.31 (s,1 H), 7.85 (d, J=8.5 Hz, 1 H), 7.56 (t, J=5.8 Hz, 1 H), 7.12 (d, J=8.5 Hz, 1 H), 3.90 (s, 3 H), 3.72 - 3.66 (m, 2 H), 3.54 - 3.47 (m, 2 H).
  • 96
  • [ 1943-83-5 ]
  • [ 98198-48-2 ]
  • 1-(5-bromo-4-methylpyridin-2-yl)-3-(2-chloroethyl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% In dichloromethane; at 0 - 20℃; for 16h; To a mixture of 5-bromo-4-methylpyridin-2-amine (2 g, 10.69 mmol) in dichloromethane (50 mL) at 0 C, was slowly added 1-chloro-2-isocyanatoethane (1.095 mL, 12.83 mmol). After stirring the mixture at rt for 16 h, it was concentrated. The crude product mixture was purified by trituration with hexanes to afford 1-(5-bromo-4-methylpyridin-2-yl)-3-(2-chloroethyl)urea (2.10 g, 77% yield) as an off-white solid. MS(ESI) m/z: 294.2 (M+H) ?H NMR (400MHz, DMSO-d6) oe 9.34 (s, 1H), 8.25 (s, 1H), 7.87 (t, J=5.8 Hz, 1H), 7.50 (s, 1H), 3.68 (t, J6.0 Hz, 2H), 3.49 (q, J=6.0 Hz, 2H), 2.30 (s, 3 H).
  • 97
  • [ 1943-83-5 ]
  • [ 944401-69-8 ]
  • 1-(5-bromo-4-fluoropyridin-2-yl)-3-(2-chloroethyl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
60.4% In dichloromethane; at 0 - 20℃; for 16h; To a mixture of <strong>[944401-69-8]5-bromo-4-fluoropyridin-2-amine</strong> (1.6 g, 8.38 mmol) indichloromethane (30 mL) at 0 C was slowly added 1-chloro-2-isocyanatoethane (0.884g, 8.38 mmol). After stirring the mixture at rt for 16 h, it was concentrated. The crudeproduct mixture was purified by trituration with hexanes to afford of 1-(5-bromo-4-fluoropyridin-2-yl)-3-(2-chloroethyl)urea (1.50 g, 60.4% yield) as an off-white solid.MS(ESI) m/z: 298.1 (M+H) ?H NMR (400MHz, DMSO-d6) oe 9.60 (s, 1H), 8.40-8.44(m, 1H), 7.60-7.65 (m, 1H), 7.48(s, 1H), 3.67 (t, J=6.0 Hz, 2H), 3.47 (q, J=6.0 Hz, 2H).
  • 98
  • [ 1943-83-5 ]
  • [ 5685-72-3 ]
  • 3-amino-5-chloro-N-(2-chloroethyl)-1H-indazole-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% In tetrahydrofuran; at 0 - 20℃; for 5.0h; General procedure: To a stirred solution of the appropriate 3-amino-1Hindazole 4a-d (6.0 mmol) in anhydrous THF (10 mL) thesolution of 2-chloroethyl isocyanate (0.7 g, 0.56 mL, 6.6mmol) in anhydrous THF (5 mL) was added dropwise at 0C. After stirring for 5 h at room temperature the precipitated solid was filtered off and the filtrate was evaporated to dryness. The solid residue thus obtained was suspended in acetonitrile (15 mL), stirred for 30 min at the room temperature and the insoluble material was filtered off. Then thefiltrate was evaporated to dryness under reduced pressure.
  • 99
  • [ 1943-83-5 ]
  • [ 16889-21-7 ]
  • 3-amino-6-chloro-N-(2-chloroethyl)-1H-indazole-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% In tetrahydrofuran; at 0 - 20℃; for 5h; General procedure: To a stirred solution of the appropriate 3-amino-1Hindazole 4a-d (6.0 mmol) in anhydrous THF (10 mL) thesolution of 2-chloroethyl isocyanate (0.7 g, 0.56 mL, 6.6mmol) in anhydrous THF (5 mL) was added dropwise at 0C. After stirring for 5 h at room temperature the precipitated solid was filtered off and the filtrate was evaporated to dryness. The solid residue thus obtained was suspended in acetonitrile (15 mL), stirred for 30 min at the room temperature and the insoluble material was filtered off. Then thefiltrate was evaporated to dryness under reduced pressure.
  • 100
  • [ 1943-83-5 ]
  • [ 7598-35-8 ]
  • 1-(2-bromopyridin-4-yl)-3-(2-chloroethyl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% at 50℃; for 5h; (1) Add 4 mL of 1-chloro-2-isocyanatoethane and 2 g of <strong>[7598-35-8]2-bromo-4-aminopyridine</strong> to a three-necked flask with a condenser tube Pyridine, the system was stirred at 50C for 5 hours,The reaction was monitored by TLC (petroleum ether:ethyl acetate=3:1). The solvent was spin-dried to give a brown oil which was purified on a silica gel column to give 1-(2-bromopyridin-4-yl)-3-(2-chloroethyl)urea, Intermediate A (light yellow solid, 1.6 g, Yield 50%)
50% at 50℃; for 5h; (1) Add 4 mL of 1-chloro-2-isocyanatoethyl ester and 2 g of <strong>[7598-35-8]2-bromo-4-aminopyridine</strong> to a three-necked flask with a condenser tube The reaction was stirred at 50 C for 5 h, and the reaction was monitored by TLC. Dry the solvent, A brown oil was obtained and purified on a silica gel column to give 1-(2-bromopyridin-4-yl)-3-(2-chloroethyl)urea. Intermediate A (light yellow solid, 1.6 g, yield 50%).
50% at 50℃; for 5h; (1) Add 4 mL to a three-necked bottle with a condenser tubeEthyl 1-chloro-2-isocyanate,2g <strong>[7598-35-8]2-bromo-4-aminopyridine</strong>, the system was stirred at 50 C for 5 h,The TLC monitors the end of the reaction. The solvent was spun dry to give a brown oil.Purified by silica gel column1-(2-bromopyridin-4-yl)-3-(2-chloroethyl)urea(Compound A, white solid, 1.6 g, 50% yield).
  • 101
  • [ 1943-83-5 ]
  • [ 59557-90-3 ]
  • C11H14BrClN2O [ No CAS ]
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