Phosgene → HCID 44553393, compound

HRID 1254043Notes

Reaction equation

HRID 1254043 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[N:11][C:10]=2[C:21]2[CH:30]=[CH:29][C:24]([C:25]([NH:27][NH2:28])=[O:26])=[CH:23][CH:22]=2)=[CH:4][CH:3]=1.[C:31](Cl)(Cl)=[O:32]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[N:11][C:10]=2[C:21]2[CH:22]=[CH:23][C:24]([C:25]3[O:26][C:31](=[O:32])[NH:28][N:27]=3)=[CH:29][CH:30]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 66986253HCID 66986253, compound

Product 1

HCID 44553393HCID 44553393, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To 4-{5-[(4-chlorophenyl)thio]-1-methyl-2-pyridin-2-yl-1H-imidazol-4-yl}benzohydrazide (Step 1 of Example 48, 120 mg, 0.27 mmol) in THF (1 mL) was added phosgene (PhMe solution, 0.55 mmol) at −78° C. After stirring at −78° C. for 60 min, the reaction was quenched with aq NaHCO3 and the product was extracted with EtOAc. The combined extracts were washed with water, brine, dried over MgSO4, filtered, and concentrated. The residue was re-crystallized in MeCN/MeOH to afford the title compound. 1H NMR (500 MHz, (CDCl3): 8.68 (d, 1H), 8.42 (broad d, 1H), 8.28 (d, 2H), 7.91 (d, 2H), 7.89 (m, 1H), 7.37 (m, 1H), 7.27 (d, 2H), 7.06 (d, 2H), 4.17 (s, 3H). LCMS: m/z 462 (M+H)+.

Workup

  1. customthe reaction was quenched with aq NaHCO3
  2. extractionthe product was extracted with EtOAc
  3. washThe combined extracts were washed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was re-crystallized in MeCN/MeOH

Sources & evidence

ORD record
ord-b1e44f198e8f40199d110d9de3d548cc
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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