Diethyl Ether → HCID 59471682, compound

HRID 78622

Reaction equation

HRID 78622 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:21]2[CH:31]=[CH:30][C:24]([C:25]([N:27]([CH3:29])[CH3:28])=[O:26])=[CH:23][CH:22]=2)=[N:6][C:7]=1[C:8](=O)[NH:9][NH:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[N:14]=1)=[O:12].CCN(C(C)C)C(C)C.BrP(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOCC>C(#N)C>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:21]2[CH:22]=[CH:23][C:24]([C:25]([N:27]([CH3:28])[CH3:29])=[O:26])=[CH:30][CH:31]=2)=[N:6][C:7]=1[C:8]1[O:12][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[N:14]=2)=[N:10][N:9]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 70579Triphenylphosphine dibromideHCID 81531DiisopropylethylamineHCID 594722274-(5-amino-6-(2-(6-aminopyridine-2-carbonyl)hydrazinecarbonyl)pyrazin-2-yl)-N,N-dimethylbenzamide

Product 1

HCID 59471682HCID 59471682, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 4-[5-amino-6-[[(6-aminopyridine-2-carbonyl)amino]carbamoyl]pyrazin-2-yl]-N,N-dimethyl-benzamide (80 mg, 0.1903 mmol) in anhydrous acetonitrile (1.600 mL) cooled in an ice bath, was added DIPEA (73.78 mg, 99.43 μL, 0.5709 mmol) followed by dibromo(triphenyl)phosphorane (104.4 mg, 0.2474 mmol) portionwise. The resulting mixture was stirred at room temperature for 30 min. The precipitate was isolated by filtration, washed with small amount of acetonitrile giving a pale yellow solid. The solid was triturated in hot acetonitrile, cooled, filtered and washed acetonitrile then ether to give the pure product (36.1 mg, 54% yield); 1H NMR (400 MHz, DMSO) d 2.98-3.02 (m, 6H), 6.53 (br s, 2H), 6.69 (m, 1.5H), 7.16 (m, 0.51H), 7.16 (m, 1H), 7.53-7.66 (m, 3H), 8.11 (m, 2H) and 8.94 (s, 1H) ppm; MS (ES+) 403.29

Workup

  1. temperaturecooled in an ice bath
  2. customThe precipitate was isolated by filtration
  3. washwashed with small amount of acetonitrile giving a pale yellow solid
  4. customThe solid was triturated in hot acetonitrile
  5. temperaturecooled
  6. filtrationfiltered
  7. washwashed acetonitrile

Sources & evidence

ORD record
ord-a8d47d8d82f849cda8c9b2bd0ee65dde
Source dataset
uspto-grants-2014_09
Patent number
US08841308B2

Linked notes

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