Phosphorus oxychloride → HCID 57503298, compound

HRID 916674Notes

Reaction equation

HRID 916674 reaction equation
[F:1][C:2]1[N:7]=[C:6]([C:8]2[N:9]([CH2:13][C:14]3[N:19]=[CH:18][N:17]=[C:16]([CH:20]([NH:22][CH:23]=O)[CH3:21])[C:15]=3[CH2:25][CH2:26][CH3:27])[CH:10]=[CH:11][N:12]=2)[CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)Cl>>[F:1][C:2]1[N:7]=[C:6]([C:8]2[N:9]([CH2:13][C:14]3[N:19]=[CH:18][N:17]4[CH:23]=[N:22][C:20]([CH3:21])=[C:16]4[C:15]=3[CH2:25][CH2:26][CH3:27])[CH:10]=[CH:11][N:12]=2)[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 57503317HCID 57503317, compound

Product 1

HCID 57503298HCID 57503298, compound

Procedure

A mixture of 215 (20 mg) and POCl3 (2 ml) is heated at reflux for 3 hours. The excess of POCl3 is removed. Ethyl acetate (10 mL) is added, and the mixture is washed with saturated NaHCO3 (5 mL), brine (5 mL), and dried over MgSO4. After evaporation of the solvent, the residue is purified by PTLC with 5% MeOH in dichloromethane to give the title product (213). 1H NMR δ (CDCL3) 0.99 (t, 3H, J=7.5 Hz), 1.55 (p, 2H, J=7.2 Hz), 2.62 (s, 3H), 2.92 (t, 2H, J=7.5 Hz), 5.92 (s, 2H), 6.87 (dd, 1H, J=8.1, 3 Hz), 7.15 (s, 1H), 7.22 (s, 1H), 7.85 (q, 1H, J=8.1 Hz), 8.06 (s, 1H), 8.14 (d, 1H, J=8.1 Hz), 8.57 (s, 1H). LC-MS: (M+1) 351.12.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 3 hours
  3. customThe excess of POCl3 is removed
  4. additionEthyl acetate (10 mL) is added
  5. washthe mixture is washed with saturated NaHCO3 (5 mL), brine (5 mL)
  6. dry with materialdried over MgSO4
  7. customAfter evaporation of the solvent
  8. customthe residue is purified by PTLC with 5% MeOH in dichloromethane

Sources & evidence

ORD record
ord-132512068f2f4d8ba018db4b1bd448c8
Source dataset
uspto-grants-2007_09
Patent number
US07271170B2

Reaction notes

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