Ammonia → HCID 54689953, compound

HRID 891273Notes

Reaction equation

HRID 891273 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[C:11]([O:22]C)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br.N>C(O)(=O)C>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[C:11]([OH:22])[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 260Hydrogen BromideHCID 9861493HCID 9861493, compound

Product 1

HCID 54689953HCID 54689953, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The product from Example 6 (1.24 g; 4 mmol) in 20 mL of acetic acid was treated with aqueous 48% HBr (25 mL). The mixture was heated at reflux for about 5 to about 8 hours (TLC analysis). The mixture was concentrated in vacuo. The product was dissolved in ethyl acetate, washed with 10% bicarbonate, brine and concentrated in vacuo. The residue was treated with diethyl ether-hexanes (2:1) and the solid was filtered to provide an almost pure product (yield: 1.16 g; 98%). 1H NMR (300 MHz, DMSO-d6) δ 5.24 (2H), 7.21 (m, 2H), 7.30 (m, 5H), 7.55 (m, 2H), 7.85 (s, 1H), 11.31 (br s, 1H). MS (DCI/NH3) m/z 296 (M+H)+, 314 (M+NH4)+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for about 5 to about 8 hours (TLC analysis)
  3. concentrationThe mixture was concentrated in vacuo
  4. dissolutionThe product was dissolved in ethyl acetate
  5. washwashed with 10% bicarbonate, brine
  6. concentrationconcentrated in vacuo
  7. additionThe residue was treated with diethyl ether-hexanes (2:1)
  8. filtrationthe solid was filtered
  9. customto provide an almost pure product (yield: 1.16 g; 98%)

Sources & evidence

ORD record
ord-b01ebc92ca57497fb0ba15a8d7c52b94
Source dataset
uspto-grants-2006_02
Patent number
US07001895B2

Reaction notes

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