302964-20-1|tert-Butyl (5-(chlorocarbonyl)thiazol-2-yl)carbamate| Ambeed

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Quality Control of [ 302964-20-1 ] Purity: 95% SDS Specification

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Product Details of [ 302964-20-1 ]

CAS No. :	302964-20-1
Formula :	C₉H₁₁ClN₂O₃S
M.W :	262.71
SMILES Code :	O=C(OC(C)(C)C)NC1=NC=C(C(Cl)=O)S1
InChI Key :	UVLGNAPYSOOUBI-UHFFFAOYSA-N
Pubchem ID :	45117870

Safety of [ 302964-20-1 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H312-H314-H332
Precautionary Statements:	P260-P261-P264-P270-P271-P280-P301+P312-P301+P330+P331-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P310-P312-P321-P322-P330-P363-P405-P501
Class:	8
UN#:	3261
Packing Group:	Ⅲ

Application In Synthesis of [ 302964-20-1 ]

* 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 [ 302964-20-1 ]

[ 302964-20-1 ] Synthesis Path-Downstream 1~18

1
[ 88-05-1 ]
[ 302964-20-1 ]
[ 302957-97-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 4007 - 4010.
[2]Journal of Medicinal Chemistry,2006,vol. 49,p. 6819 - 6832.

2
[ 87-63-8 ]
[ 302964-20-1 ]
[ 302964-06-3 ]

Yield	Reaction Conditions	Operation in experiment
40%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 30℃; for 25.5h;	Into a clean and dry 3L 4-neck round bottom flask connected to a mechanical stirrer,condenser and thermometer socket is charged with <strong>[302964-20-1]2-tert-butoxycarbonylamino-thiazole-5-carboxylic acid chloride</strong> (4) crude (27.5 g) and dichloromethane (750 mL) under stirring. Cooled the reaction mass to 0-5 C and add 2-chloro-6-methylaniline (22.2 g) to the reaction mass at 0-5 C within 30-45 min period. Added DiPEA to the reaction mass at 0-5 C in 30-45 min period, raised the reaction mass temperature to 25-30 C and stirred the reaction mass at 25-30 C for 24 h. After TLC compliance distilled-off the solvent completely under plant vacuum at the temperature not crossing 50 C and Charge 2 N HCl (250 mL) to the reaction mass, Stirred for 15-30 min. Transferred the reaction mass into a Buchner funnel and flask kept under plant vacuum. The wet cake is washed with 500mL of water and dried the above-wet material in the dryer at temperature 60-65 C for 10-12 h. Purification: Into a clean and dry 3.0 L 4-neck round bottom flask connected to a mechanical stirrer, condenser, thermometer socket is charging with 2-tert-butoxy-carbonyl-amino-N-(2-chloro-6-methylphenyl)-5-thiazolecarboxamide crude, methanol and isopropyl ether under stirring at 25- 30 C. Raised the reaction mass temperature to 60-65 C and stirred the reaction mass at 60-65 C for 45-60 min. Cooled the reaction mass temperature to 25-30 C and transferred the reaction mass into a Buchner funnel and flask kept under plant vacuum. Washed the wet cake with 20.0 mL of methanol and dried the wet material in dryer at 60-65 C for 4-6 h to furnish 16.0 g of the title compound with purity above 95 %. Cream colour solid; Elemental analysis C16H18N3O3SClcalcd (found) %: C 52.24 (52.12), H 4.93 (5.05), N 11.42 (11.31),O 13.05 (13.25), S 8.72 (8.83). IR (KBr, numax, cm-1): 3423.42-3276.87, 3162.67, 2928.46, 1724.90, 1632.68-1566, 1522.80,775.21; 1H NMR (400 MHz, DMSO-d6): delta1.504 (s, 9H, -3CH3),2.225 (s, 3H, -CH3), 7.262-7.301 (t, 2H, ArH), 7.389-7.412(m, 1H, ArH), 8.204 (s, 1H, ArH), 10.017 (s, 1H, -NH), 11.847(s, 1H, -NH); 13C NMR (100 MHz, DMSO-d6): delta163.220, 159.74,152.91, 141.27, 139.02, 133.31, 132.57, 129.34, 128.64, 127.28,126.62, 82.33, 28.06, 18.45; ESI-MS (m/z): 368.21 (M+1),370.18 (M+3)
	With N-ethyl-N,N-diisopropylamine; In dichloromethane;	[00106] Compound 8 was made using by adapfing the synthesisdsdosed n J.Med.Chem. 2006, 6819. Synthesis of amde 5 was accomphshedn two steps, starting from compound 1. Compound I was converted to acidchorde 2 using oxay chorde n dchoromethane (DCM). Formafion of theacd chorde was confirmed by quenching an aquot n methano (MeOH);LCMS anayss ndcated the presence of the corresponding methy? ester 3 n>90%. Add Won of 2 to a mixture of excess anWne 4 and dsopropy ethyamne(DPEA) gave good conversion to amine 5. After fHtehng the sohds off thisafforded 1.15 g (40%) amde 5 n high purIty. Remova of the Boc-group using tr[fluoroacefic acid (TFA) gave good conversion to amine 6. Amine 6 was converted to compound 8 n the presence of compound 7 and sodium t-butoxde (NaOBu-t).
16.0 g	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 30℃;	Into a clean and dry 3.0.L 4-neck RB flask charged 2- tert-Butoxycarbonylamino- thiazole-5-carboxylic acid chloride crude (28 gm) and methylene chloride (750 (0089) ml) under stirring, cooled the reaction mass to temperature to 0-5C. Added 2- Chloro-6-methyl aniline (23gm) to the reaction mass at temperature 0- 5C within 30-45 min period. Diisopropyl ethylamine (55 gm) was added to the reaction mass at temperature 0-5 C in 30-45 min period, reaction mass temperature was raised to 25-30C and maintained for 24 hrs, after completion of the reaction, distilled off the solvent completely under plant vacuum at temperature not crossing 50C. (0090) charged 2 HC1 to the reaction mass and stirred for 15-30 min, transferred the (0091) reaction mass into a buchner funnel and flask kept under plant Vacuum. Wet cake was washed with 250.0 ml of water and suck dried thoroughly for 30-45 min, wet material was transferred into a clean and dry petridish. Dried the above wet (0092) material in drier at temperature 60-65 C forlO-12 hrs. (0093) Weight: 20gm f) purification of 2-tert-butoxy- carbonyl amino-N-(2-chloro-6- methylphenyl)-5-thiazolecarboxamide (0095) Into a clean and dry 3.0.L 4-neck RB flask charged 2-tert-butoxy- carbonyl (0096) amino-N-(2-chloro-6-methylphenyl)-5-thiazolecarboxamide crude(20gm) , (0097) methanol (250ml, Lot-1) and (0098) Isopropyl ether(200ml) under stirring at temperature 25- 30C, reaction mass (0099) temperature was raised to 60-65C and maintained for 45-60 min. cooled the (0100) reaction mass temperature to 25-30C and transferred the reaction mass into a (0101) buchner funnel and flask kept under plant vacuum. Washed the wet cake with (0102) 20.0 ml of methanol (LOT-II)and suck dried for 10-15min, and dried the (0103) compound in drier at temperature 60-65 C for 4-6 hrs. (0104) Weight: 16.0 g

References: [1]Asian Journal of Chemistry,2018,vol. 30,p. 1621 - 1628.
[2]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 4007 - 4010.
[3]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 6061 - 6066.
[4]Journal of Medicinal Chemistry,2006,vol. 49,p. 6819 - 6832.
[5]ARKIVOC,2010,vol. 2010,p. 32 - 38.
[6]Patent: WO2017/100703,2017,A1 .Location in patent: Paragraph 00105; 00106.
[7]Synthetic Communications,2017,vol. 47,p. 1610 - 1621.
[8]Patent: WO2018/100585,2018,A1 .Location in patent: Page/Page column 8-9.

3
[ 302964-02-9 ]
[ 302964-20-1 ]

Yield	Reaction Conditions	Operation in experiment
96%	With sodium hydroxide; In tetrahydrofuran; methanol; water; at 20℃; for 24h;	[0405] A stirred solution of ethyl-2-tert-butoxycarbonyloxyamino-4-methyl-thiazole-5-carboxylate (1.1 g, 4.2 mmol) in tetrahydrofuran-methanol (80 mL, 1:1) was treated with a 6N aq. NaOH solution (20 mL, 120 mmol). The mixture was stirred at rt for 24 h. Most of THF and methanol were removed by distillation under reduced pressure and the aq. Solution was acidified with 6 N aq. HCl solution (22 mL). The precipitated solid was filtered, washed with water and ether, air dried followed by drying in vacuo to obtain the title acid (940 mg, 96%) as an off-white solid.
	With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20℃; for 1h;	To an cooled (0 C) dichloromethane (4 mL) solution of 2-[(tert- butoxycarbonyl)amino]-l,3-thiazole-5-carboxylic acid (0.30 g) was added a solution of oxalyl chloride (0.13 mL) in dichloromethane (1 mL). One drop of N,N- dimethylformamide was added and the mixture stirred at room temperature for 1 hour. The reaction mixture was concentrated and the residue dissolved in acetonitrile (5 mL). To the cooled (0 C) acetonitrile solution, a 2 M solution of (trimethylsilyl)diazomethane in tiexanes (1.23 mL) was added and the mixture stirred at 0 C for 1 hour. To the reaction mixture, a solution of 33 wt. % hydrogen bromide in acetic acid (0.20 mL) was added and the mixture stirred at 0 C for a further 20 minutes. A saturated aqueous solution of sodium hydrogen carbonate ( 0 mL) was added followed by extraction with ethyl acetate. The combined organic layers were washed with brine, dried and concentrated to give the crude title compound having the following physical properties (0.37 g). LC MS fR 1.92 minutes; MS (ES+) m/z 265 and 267 (M-C(CH3)3+H) a.
	With oxalyl dichloride; In dichloromethane;	[00106] Compound 8 was made using by adapfing the synthesisdsdosed n J.Med.Chem. 2006, 6819. Synthesis of amde 5 was accomphshedn two steps, starting from compound 1. Compound I was converted to acidchorde 2 using oxay chorde n dchoromethane (DCM). Formafion of theacd chorde was confirmed by quenching an aquot n methano (MeOH);LCMS anayss ndcated the presence of the corresponding methy? ester 3 n>90%. Add Won of 2 to a mixture of excess anWne 4 and dsopropy ethyamne(DPEA) gave good conversion to amine 5. After fHtehng the sohds off thisafforded 1.15 g (40%) amde 5 n high purIty. Remova of the Boc-group using tr[fluoroacefic acid (TFA) gave good conversion to amine 6. Amine 6 was converted to compound 8 n the presence of compound 7 and sodium t-butoxde (NaOBu-t).

	With thionyl chloride; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; at 25 - 30℃;	Into a clean and dry 1 L 4-neck round bottom flask connected to a mechanical stirrer, condenser, thermometer socket is charged with 2-tert-butoxy-carbonylaminothiazole-5-carboxylic acid (3) (25.0 g), THF (1 L) and DMF (1 mL) at 25-30 C under stirring. Charged thionyl chloride (22.5 mL of thionyl chloride dissolved in 125 mL of dichloromethane) to the mass at 25-30 C. Maintained the reaction mass at 25-30 C for 4-6 h and after TLC compliance, distilled-off solvent completely under plant vacuum at the temperature not crossing 50 C. Charged THF (125 mL) to the reaction mass, stirring the mass for 10-15 min and distilled-off solvent completely under plant vacuum at the temperature not crossing 40 C. Charged 125 mL of dichloromethane to the reaction mass, stirring the mass for 10-15 min and distilled-off solvent completely under plant vacuum at the temperature not crossing 40 C to furnish 27-28 g of crude compound.
	With thionyl chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; at 25 - 30℃;	Into a clean and dry 1.0. L 4-neck RB charged 2- tert-butoxycarbonylamino- thiazole-5-carboxylic acid(25gm),and THF(lltr, Lot-I) and DMF(10 ml) at (0075) temperature 25-30C under stirring. Charged thionyl chloride (22.5 ml, dissolved (0076) in 125ml of dichloromethane-Lot-I) to the mass at temperature 25-30C, (0077) maintained the mass at temperature 25-30C for 4-6hrs., after completion of the (0078) reaction, distilled-off solvent completely under plant vacuum at temperature not (0079) crossing 50C, charged THF (125ml, Lot-II) to reaction mass.Stirr the mass for (0080) 10-15 min. Distilled-off solvent completely under plant vacuum at temperature not crossing 40C, charged dichloromethane (125ml, Lot-II) to reaction mass. (0081) Stirred the mass for 10-15 min.Distilled-off solvent completely under plant (0082) vacuum at temperature not crossing 40C. Distilled-off solvent completely under (0083) plant vacuum at temperature not crossing 60C. Crude acid chloride is directly (0084) taken to next stage in-situ. (0085) Weight: 27 gm

References: [1]Patent: US2004/54186,2004,A1 .Location in patent: Page 23; 93.
[2]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 4007 - 4010.
[3]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 6061 - 6066.
[4]Journal of Medicinal Chemistry,2006,vol. 49,p. 6819 - 6832.
[5]ARKIVOC,2010,vol. 2010,p. 32 - 38.
[6]Patent: WO2013/93484,2013,A1 .Location in patent: Page/Page column 253.
[7]Patent: WO2017/100703,2017,A1 .Location in patent: Paragraph 00105; 00106.
[8]Synthetic Communications,2017,vol. 47,p. 1610 - 1621.
[9]Asian Journal of Chemistry,2018,vol. 30,p. 1621 - 1628.
[10]Patent: WO2018/100585,2018,A1 .Location in patent: Page/Page column 8.

4
[ 87-62-7 ]
[ 302964-20-1 ]
[ 934193-04-1 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6819 - 6832.

5
[ 24424-99-5 ]
[ 302964-20-1 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6819 - 6832.
[2]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 4007 - 4010.
[3]Synthetic Communications,2017,vol. 47,p. 1610 - 1621.
[4]Asian Journal of Chemistry,2018,vol. 30,p. 1621 - 1628.
[5]Patent: WO2018/100585,2018,A1 .

6
[ 302964-01-8 ]
[ 302964-20-1 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6819 - 6832.
[2]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 4007 - 4010.
[3]Asian Journal of Chemistry,2018,vol. 30,p. 1621 - 1628.
[4]Patent: WO2018/100585,2018,A1 .

7
[ 302964-20-1 ]
[ 302957-97-7 ]

References: [1]Patent: US2004/54186,2004,A1 .Location in patent: Page 23; 112.

8
[ 17430-98-7 ]
[ 302964-20-1 ]
[ 1152210-14-4 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 20℃; for 8h;	To 10 mL of THF were added 0.8 g of 2- [(1,1- dimethylethoxy) carbonylamino] -5-carboxylic acid chloride, 0.27 g of (IS) -1-cyclohexylethylamine and 0.80 g of triethylamine, and the mixture was stirred at room temperature for 8 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with an aqueous saturated sodium bicarbonate and saturated brine successively, then dried over magnesium sulfate, and concentrated under reduced pressure. The resultant solid was washed with hexane to obtain 0.94 g of N- [ (IS) -1-cyclohexylethyl] -2- [ (1, 1- dimethylethoxy) carbonylamino] thiazole-5-carboxamide .N- [ (IS) -1-cyclohexylethyl] -2- [(1,1- dimethylethoxy) carbonylamino] thiazole-5-carboxamide1H-NMR (CDCl3) delta: 0.97-1.44 (8H, m) , 1.48-1.81 (15H, m) ,4.00-4.05 (IH, m) , 5.48 (IH, d, J = 8.9 Hz), 7.84 (IH, s), 10.49 (IH, br s) .

References: [1]Patent: WO2009/66790,2009,A1 .Location in patent: Page/Page column 46.

9
[ 904733-73-9 ]
[ 302964-20-1 ]
[ 1152210-12-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 20℃; for 8h;	To 10 mL of THF were added 0.80 g of 2- [(1,1- dimethylethoxy) carbonylamino] thiazole-5-carboxylic acid chloride, 0.33 g of 1-cyclobutylethylamine hydrochloride and 0.80 g of triethylamine, and the mixture was stirred at room temperature for 8 hours. Diluted hydrochloric acid was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water and brine successively, dried over magnesium sulfate, and then concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain 0.75 g of N- (1-cyclobutylethyl) -2- [ ( 1 , 1-dimethylethoxy) carbonylamino] thiazole-5-carboxamide . N- (1-cyclobutylethyl) -2- [(1,1- dimethylethoxy) carbonylamino] thiazole-5-carboxamide1H-NMR (CDCl3) delta: 1.11 (3H, d, J = 6.3 Hz), 1.58 (9H, s), <n="42"/>1.74-2.07 (6H, m) , 2.24-2.35 (IH, m) , 4.07-4.16 (IH, m) , 5.38 (IH, d, J = 8.5 Hz) , 7.83 (IH, s) , 10.63 (IH, br s) .

References: [1]Patent: WO2009/66790,2009,A1 .Location in patent: Page/Page column 40-41.

10
[ 302964-20-1 ]
[ 18107-18-1 ]
[ 1445866-34-1 ]

Yield	Reaction Conditions	Operation in experiment
0.37 g		To an cooled (0 C) dichloromethane (4 mL) solution of 2-[(tert- butoxycarbonyl)amino]-l,3-thiazole-5-carboxylic acid (0.30 g) was added a solution of oxalyl chloride (0.13 mL) in dichloromethane (1 mL). One drop of N,N- dimethylformamide was added and the mixture stirred at room temperature for 1 hour. The reaction mixture was concentrated and the residue dissolved in acetonitrile (5 mL). To the cooled (0 C) acetonitrile solution, a 2 M solution of (trimethylsilyl)diazomethane in tiexanes (1.23 mL) was added and the mixture stirred at 0 C for 1 hour. To the reaction mixture, a solution of 33 wt. % hydrogen bromide in acetic acid (0.20 mL) was added and the mixture stirred at 0 C for a further 20 minutes. A saturated aqueous solution of sodium hydrogen carbonate ( 0 mL) was added followed by extraction with ethyl acetate. The combined organic layers were washed with brine, dried and concentrated to give the crude title compound having the following physical properties (0.37 g). LC MS fR 1.92 minutes; MS (ES+) m/z 265 and 267 (M-C(CH3)3+H) a.

References: [1]Patent: WO2013/93484,2013,A1 .Location in patent: Page/Page column 253.

11
[ 1444001-34-6 ]
[ 302964-20-1 ]
ethyl 1-(4-((S)-5-((2-((tert-butoxycarbonyl)amino)thiazole-5-carboxamido)methyl)-2-oxooxazolidin-3-yl)phenyl)piperidine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	With triethylamine; In dichloromethane; at 0 - 20℃; for 15h;	General procedure: Solution of <strong>[302964-20-1]tert-butyl (5-(chlorocarbonyl)thiazol-2-yl)carbamate</strong> (1.2 eq.) in dichloromethane (0.35 M) was added dropwise to a stirred solution of starting compound (5a-e) and triethylamine (2 eq.) in dichloromethane (0.075 M) at 0 C. The reaction mixture was stirred for 15 h at room temperature followed by removal of solvent under reduced pressure to obtain a crude product, which was purified by flash column chromatography using dichloromethane/methanol (19/1) or EtOAc as eluant.