Triphenylphosphine dibromide → HCID 59472114, compound

HRID 331507Notes

Reaction equation

HRID 331507 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([NH:11][NH:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][N:22]([CH3:30])[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:17][CH:16]=2)=[O:14])=O)=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.C(N(C(C)C)CC)(C)C.BrP(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(#N)C>[NH2:1][C:2]1[C:3]([C:9]2[O:14][C:13]([C:15]3[CH:16]=[CH:17][C:18]([CH2:21][N:22]([CH3:30])[C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:28])[CH3:26])=[CH:19][CH:20]=3)=[N:12][N:11]=2)=[N:4][C:5]([Br:8])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 70579Triphenylphosphine dibromideHCID 81531DiisopropylethylamineHCID 59472138Tert-butyl 4-(2-(3-amino-6-bromopyrazine-2-carbonyl)hydrazinecarbonyl)benzyl(methyl)carbamate

Product 1

HCID 59472114HCID 59472114, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

tert-butyl N-[[4-[[(3-amino-6-bromo-pyrazine-2-carbonyl)amino]carbamoyl]phenyl]methyl]-N-methyl-carbamate (7.66 g, 15.98 mmol) was dissolved in dry acetonitrile (114.9 mL) and cooled in an ice bath and put under a nitrogen atmosphere. Diisopropylethylamine (6.196 g. 8.350 mL, 47.94 mmol) was added via a syringe followed by dibromo(triphenyl)phosphorane (8.767 g, 20.77 mmol) portion wise. Reaction mixture started to precipitate out therefore left to stir for 45 minutes in an ice bath and isolated precipitated product by filtration as a beige powder (4.5 g). This material was then sonicated, triturated in acetonitrile, filtered and dried to give the sub-titled compound as yellow solid. (3.17 g, 40.9%). 1H NMR (400 MHz, DMSO-d6) δ 1.38-1.45 (br d, 9H), 2.80 (s, 3H), 4.45 (s, 2H), 7.48-7.51 (br s, 2H), 7.80 (br s, 2H), 8.10-8.20 (m, 2H), 8.45 (s, 1H) ppm; LC/MS m/z 463.1, 464.2 [M+H]+.

Workup

  1. temperaturecooled in an ice bath
  2. customReaction mixture
  3. customto precipitate
  4. waitout therefore left
  5. customisolated
  6. customprecipitated product
  7. filtrationby filtration as a beige powder (4.5 g)
  8. customThis material was then sonicated
  9. customtriturated in acetonitrile
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-4d88a8ec8b264274b51187ea51d92d9e
Source dataset
uspto-grants-2014_11
Patent number
US08877759B2

Reaction notes

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