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Structure of 63744-29-6

Chemical Structure| 63744-29-6

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Product Details of [ 63744-29-6 ]

CAS No. :63744-29-6
Formula : C5H3BrN4
M.W : 199.01
SMILES Code : BrC1=CN=CC2=NN=CN21
MDL No. :MFCD13193617
InChI Key :CTDOUHOODJJYQH-UHFFFAOYSA-N
Pubchem ID :71748557

Safety of [ 63744-29-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P280-P305+P351+P338-P310

Application In Synthesis of [ 63744-29-6 ]

* 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 [ 63744-29-6 ]

[ 63744-29-6 ] Synthesis Path-Downstream   1~5

  • 2
  • [ 63744-29-6 ]
  • 4-methylbenzyl (3S,4R)-4-(aminomethyl)-3-fluoropiperidine-1-carboxylate hydrochloride [ No CAS ]
  • (3S,4R)-4-methylbenzyl 4-(([1,2,4]triazolo[4,3-a]pyrazin-5-ylamino)methyl)-3-fluoropiperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
19% With dicyclohexyl-(2?,4?,6?-triisopropyl-3,6-dimethoxy-[1,1?-biphenyl]-2-yl)phosphine; chloro[2-(dicyclohexylphosphino)-3 ,6-dimethoxy-2?,4?, 6?-triisopropyl- 1,1?-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); caesium carbonate; In tert-butyl alcohol; at 100 - 120℃;Sealed tube; Inert atmosphere; EXAMPLE 1.29. (3S,4 ?)-4-methylbenzyl 4-(([l,2,4]triazolo[4,3-a]pyrazin-5-ylamino)methyl)-3-fluoro- piperidine-l-carboxylate (El-2.2). [0267] A mixture of 5-bromo-[l,2,4]triazolo[4,3-a]pyrazine (280 mg, 1.40 mmol), (3S,4R)- 4- methylbenzyl 4-(aminomethyl)-3-fluoropiperidine-l-carboxylate hydrochloride (532 mg, 1.68 mmol), Brettphos precatalyst (30 mg), Brettphos (30 mg), and Cs2C03 (2.28 g, 7.0 mmol) in t-BuOH (7 mL) was heated to 120C in the sealed tube under N2 atmosphere. After stirring overnight at 100C, the mixture was cooled down to room temperature and concentrated under vacuum. The concentrate was partitioned into DCM and water. The aqueous phase was extracted with DCM. The combined organic phases were washed with water, brine, dried over Na2S04 and concentrated. The concentrate was purified by column chromatography over silica gel (eluent: 100% ethyl acetate) to afford the title compound as a brown powder (106 mg, 19%). MS (ESI) calcd for C2oH23FN602: 398.2; found: 399.3[M+H]. *H NMR (400 MHz, CDCI3) delta 8.72 (s, 1H), 7.45-7.30 (m, 4H), 7.26-7.20 (m, 2H), 7.20-7.12 (m, 2H), 6.68-6.52 (m, 1H), 5.10 (br s, 2H), 4.95-4.65 (m, 1H), 4.63-4.16 (m, 2H), 3.77-3.62 (m, 2H), 3.02-2.67 (m, 2H), 2.35 (s, 3H), 2.25-1.97 (m, 1H), 1.65-1.46 (m, 2H).
  • 3
  • [ 63744-29-6 ]
  • (3R,4S)-4-methylbenzyl 4-(aminomethyl)-3-fluoropiperidine-1-carboxylate hydrochloride [ No CAS ]
  • (3R,4S)-4-methylbenzyl 4-(([1,2,4]triazolo[4,3-a]pyrazin-5-ylamino)methyl)-3-fluoropiperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% With dicyclohexyl-(2?,4?,6?-triisopropyl-3,6-dimethoxy-[1,1?-biphenyl]-2-yl)phosphine; chloro[2-(dicyclohexylphosphino)-3 ,6-dimethoxy-2?,4?, 6?-triisopropyl- 1,1?-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); caesium carbonate; In tert-butyl alcohol; at 100℃;Sealed tube; Inert atmosphere; EXAMPLE 1.30. (3 ?,4S)-4-methylbenzyl 4-(([l,2,4]triazolo[4,3-a]pyrazin-5-ylamino)methyl)-3-fluoro- piperidine-l-carboxylate (E2-2.2). [0269] A mixture of 5-bromo-[l,2,4]triazolo[4,3-a]pyrazine (160 mg, 0.80 mmol), (3R,4S)-4- methylbenzyl 4-(aminomethyl)-3-fluoropiperidine-l-carboxylate hydrochloride (306 mg, 0.96 mmol), Brettphos precatalyst (20 mg), Brettphos (20 mg), and Cs2C03 (789 mg, 2.4 mmol) in t-BuOH (6 mL) was heated to 100C in the sealed tube under N2 atmosphere. After stirring overnight at 100C, the mixture was cooled down to room temperature and concentrated under vacuum. The concentrate was partitioned into DCM and water. The aqueous phase was extracted with DCM. The combined organic phases were washed with water, brine, dried over Na2S04 and concentrated. The concentrate was purified by column chromatography over silica gel (eluent: 100% ethyl acetate) to afford the title compound as a brown powder (92 mg, 28%). MS (ESI) calcd for C2oH23FN602: 398.2; found: 399.3[M+H]. *H NMR (400 MHz, CDCI3) delta 8.72 (s, 1H), 7.41 (d, J = 4.4 Hz, 1H), 7.34 (d, J = 4.4 Hz, 1H), 7.25 (d, J = 7.2 Hz, 2H), 7.17 (d, J = 7.2 Hz, 2H), 6.58 (br s, 1H), 5.09 (br s, 2H), 4.90-4.69 (m, 1H), 4.65-4.15 (m, 2H), 3.75-3.60 (m, 2H), 3.02-2.70 (m, 2H), 2.35 (s, 3H), 2.24-2.08 (m, 1H), 1.75- 1.65 (m, 2H).
  • 4
  • [ 63744-29-6 ]
  • (3S,4R)-tert-butyl 4-(aminomethyl)-3-fluoropiperidine-1-carboxylate [ No CAS ]
  • (3S,4R)-tert-butyl 4-(([1,2,4]triazolo[4,3-a]pyrazin-5-ylamino)methyl)-3-fluoropiperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With N-ethyl-N,N-diisopropylamine; In ethylene glycol; at 110℃; for 7.0h;Sealed tube; Inert atmosphere; Step 1: (3S,4 ?)-tert-butyl 4-(([l,2,4]triazolo[4 -a]pyrazin-5-ylamino)methyl)-3-fluoropiperidine- 1-carboxylate [0185] A mixture of 5-bromo-[l,2,4]triazolo[4,3-a]pyrazine (102 mg, 0.51 mmol), (3S,4R)-tert-butyl 4- (aminomethyl)-3-fluoropiperidine-l-carboxylate (80 mg , 0.34 mmol) and DIPEA (1.2 mL, 1.0 mmol) in ethylene glycol (2 mL) was heated to 110 C in the sealed tube for 7 hr under N2 atmosphere. The mixture was allowed to cool to rt and concentrated. The concentrate was partitioned into DCM and water. The organic phase was washed with water, brine, dried over Na2S04 and concentrated. The concentrate was purified by column chromatography over silica gel (MeOH/DCM=50/l) to afford the title compound as an off-white powder (60 mg, 50%). MS (ESI) calcd for C16H23FN602: 350.2; found: 351.3[M+H]. 1H NMR (400 MHz, CDCI3) delta 8.72 (s, 1H), 7.41 (d, J = 4.8 Hz, 1H), 7.34 (d, J = 4.8 Hz, 1H), 6.55-6.47 (m, 1H), 4.90-4.65 (m, 1H), 4.62-4.35 (m, 1H), 4.33-4.05 (m , 1H), 3.74-3.64 (m, 2H), 2.96-2.62 (m, 2H), 2.24 -2.04 (m, 1H), 1.73-1.58 (m, 1H), 1.46 (s, 9H).
  • 5
  • [ 63744-29-6 ]
  • (-)-R-tert-butyl 4-(aminomethyl)-3,3-difluoropiperidine-1-carboxylate [ No CAS ]
  • R-tert-butyl 4-(([1,2,4]triazolo[4,3-a]pyrazin-5-ylamino)methyl)-3,3-difluoropiperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 130℃; A mixture of R-tert-butyl 4-(aminomethyl)-3,3-difluoropiperidine-1-carboxylate (300 mg, 1.20mmol), <strong>[63744-29-6]5-bromo-[1,2,4]triazolo[4,3-a]pyrazine</strong> (356 mg, 1.80 mmol) and DIPEA (0.42 mL, 2.40 mmol in NMP (9 mL) was heated to 130C with stirring overnight. The orange solution was allowed to cool down to rt and diluted with ethyl acetate. The organic phase was washed with water, brine, dried over Na2SO4 and concentrated under vacuum. The concentrate was purified by column chromatography over silica gel (hexane/ethyl acetate = 1/3) to afford the title compound as a yellow powder (210 mg, 48%). 1H NMR (400 MHz, CDCI3) 6 9.25 (s, 1H), 8.85 (s, 1H), 7.27 (s, 1H), 6.17-6.01 (m, 1H), 4.51-4.17 (m, 2H), 3.93-3.84 (m, 1H), 3.52-3.44 (m, 1H), 3.11-2.71 (m, 2H), 2.52-2.37 (m, 1H), 2.03-1.92 (m, 1H), 1.73-1.63 (m, 1H), 1.48 (s, 9H).
 

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