Nitrogen → HCID 86690313, compound

HRID 1428691Notes

Reaction equation

HRID 1428691 reaction equation
[CH2:1]([O:3][C:4](=[O:34])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:15]2=[N:16][C:17]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)[N:19]=[C:14]2[CH:13]=[CH:12]1)[CH3:2].N#N.O=P(Cl)(Cl)Cl.CN([CH:45]=[O:46])C>>[CH:45]([C:13]1[C:14]2[C:15](=[N:16][C:17]([C:27]3[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=3)=[C:18]([C:20]3[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=3)[N:19]=2)[N:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:34])[CH:12]=1)=[O:46]

Participants

5

Reactant 4

HCID 947NitrogenHCID 6228DimethylformamideHCID 24813Phosphorus oxychloride2×HCID 71657498HCID 71657498, compound2×

Product 1

HCID 86690313HCID 86690313, compound

Procedure

A mixture comprising 7-(2,3-di-p-tolyl-pyrrolo[2,3-b]pyrazin-5-yl)-heptanoic acid ethyl ester (Intermediate B) (479 mg, 1.051 mmol) in anhydrous DMF (1 ml) was degassed with N2 and treated dropwise with POCl3 (0.147 ml, 1.577 mmol). The mixture was stirred at room temperature for 3 hours and treated with a further portion of POCl3 (0.147 ml, 1.577 mmol). After stirring at RT for 16 hours, the mixture was partitioned between water (100 ml) and EtOAc (20 ml) and the pH of the bi-phasic solution was adjusted to pH 8-9 using sat. NaHCO3 solution. The aqueous portion was extracted with EtOAc (×3) and the combined organic extract were washed with water (×1), brine (×1), dried over MgSO4 and filtered and concentrated under reduced pressure to afford the titled compound as a brown oil;

Workup

  1. stirringAfter stirring at RT for 16 hours
  2. customthe mixture was partitioned between water (100 ml) and EtOAc (20 ml)
  3. extractionThe aqueous portion was extracted with EtOAc (×3)
  4. extractionthe combined organic extract
  5. washwere washed with water (×1), brine (×1)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3bfc2465941b4c728a9360253b56c9da
Source dataset
uspto-grants-2015_01
Patent number
US08937069B2

Reaction notes

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