Hydrogen Bromide → HCID 86690298, compound

HRID 1854803Notes

Reaction equation

HRID 1854803 reaction equation
C(OC(=O)[NH:10][CH2:11][C:12]([N:15]1[C:19]2=[N:20][CH:21]=[N:22][C:23]([NH2:24])=[C:18]2[C:17]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:16]1)([CH3:14])[CH3:13])C1C=CC=CC=1.[BrH:32].CCOCC>C(O)(=O)C>[BrH:32].[NH2:10][CH2:11][C:12]([N:15]1[C:19]2=[N:20][CH:21]=[N:22][C:23]([NH2:24])=[C:18]2[C:17]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:16]1)([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 66779959HCID 66779959, compound

Product 1

HCID 86690298HCID 86690298, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Compound 1D (85 mg, 0.2 mmol) was treated with 1 mL of 33% solution of HBr in glacial acetic acid. The reaction was stirred at room temperature for 1 hour. Dry ether was then added to the mixture leading to the formation of a precipitate. It was collected by filtration, rinsed thoroughly with Et2O and dried. 50 mg of the compound were redissolved in 50 mL of water and freeze dried for two days. A white solid was obtained. 1H NMR (ppm, DMSO-d6): δ 1.73 (s, 6H), 2.34 (s, 3H), 3.59 (br q, J=5.67 Hz, 2H), 7.33 (d, J=7.89 Hz, 2H), 7.53 (d, J=8.07 Hz, 2H), 7.95 (br s, 3H), 8.40 (s, 1H). 13C NMR (ppm, DMSO-d6): δ 20.93, 24.83, 46.51, 61.41, 98.47, 128.33, 128.76, 129.80, 138.82, 144.85, 149.49, 152.83, 154.21. LCMS (+esi): 297 (M-Br−).

Workup

  1. filtrationIt was collected by filtration
  2. washrinsed thoroughly with Et2O
  3. customdried
  4. dissolution50 mg of the compound were redissolved in 50 mL of water
  5. customfreeze dried for two days
  6. customA white solid was obtained

Sources & evidence

ORD record
ord-72ceb9b5888e4462a6aeeef6abb2e32f
Source dataset
uspto-grants-2015_02
Patent number
US08962830B2

Reaction notes

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