HCID 58958171, compound → HCID 58958108, compound

HRID 914989Notes

Reaction equation

HRID 914989 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([NH:12][C:13]2[CH:14]=[C:15]([CH:33]=[CH:34][CH:35]=2)[C:16]([NH:18][NH:19][C:20](=[O:32])[CH2:21][N:22]2[CH2:31][CH2:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:23]2)=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1>P(Cl)(Cl)(Cl)=O>[CH2:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:30][CH2:31][N:22]1[CH2:21][C:20]1[O:32][C:16]([C:15]2[CH:14]=[C:13]([NH:12][C:10]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[N:3]=[C:2]([CH3:1])[CH:11]=3)[CH:35]=[CH:34][CH:33]=2)=[N:18][N:19]=1

Participants

3

Reactant 1

HCID 58958171HCID 58958171, compound

Product 1

HCID 58958108HCID 58958108, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A mixture of 92 (195 mg, 0.42 mmol) in phosphorous oxychloride (0.5 mL) was heated overnight before mixing cautiously with ice water (2 mL). The mixture was extracted with 7:3 CH2Cl2/MeOH, and the organic layer was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, gradient elution) to give the desired product as a pale yellow solid (69 mg, 37%).

Workup

  1. temperaturewas heated overnight
  2. extractionThe mixture was extracted with 7:3 CH2Cl2/MeOH
  3. dry with materialthe organic layer was dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (SiO2, gradient elution)

Sources & evidence

ORD record
ord-72d27777a9074be5bb571e72f851a389
Source dataset
uspto-grants-2007_09
Patent number
US07265122B2

Reaction notes

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