Triethylamine → HCID 44553731, compound

HRID 1254044Notes

Reaction equation

HRID 1254044 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](N1C=CN=C1)(N1C=CN=C1)=[S:32].C(N(CC)CC)C>ClCCl>[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](=[S:32])[NH:28][N:27]=3)=[CH:29][CH:30]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 802641,1'-ThiocarbonyldiimidazoleHCID 66986253HCID 66986253, compound

Product 1

HCID 44553731HCID 44553731, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-{5-[(4-chlorophenyl)thio]-1-methyl-2-pyridin-2-yl-1H-imidazol-4-yl}benzohydrazide (Step 1 of Example 48, 50 mg, 0.115 mmol) and 1,1′-carbonothioylbis(1H-imidazole) (41 mg, 0.23 mmol) in dichloromethane (1 mL) was added triethylamine (46 mg, 0.46 mmol) at rt. After 1 h, the reaction was quenched with aq NaHCO3 and the product was extracted 3 times with EtOAc. The combined extracts were concentrated, and the residue was subjected to reverse phase HPLC. The fractions containing the product were collected and concentrated. The residue was diluted with EtOAc, washed with aq NaHCO3, water, and brine. The organic layer was dried over MgSO4, filtered, and concentrated to afford the title compound. 1H NMR (500 MHz, (CDCl3): 8.65 (d, 1H), 8.38 (broad d, 1H), 8.36 (d, 2H), 8.19 (s, 1H), 8.03 (d, 2H), 7.84 (m, 1H), 7.38 (m, 1H), 7.27 (d, 2H), 7.07 (d, 2H), 4.16 (s, 3H). LCMS: m/z 478 (M+H)+.

Workup

  1. customthe reaction was quenched with aq NaHCO3
  2. extractionthe product was extracted 3 times with EtOAc
  3. concentrationThe combined extracts were concentrated
  4. additionThe fractions containing the product
  5. customwere collected
  6. concentrationconcentrated
  7. additionThe residue was diluted with EtOAc
  8. washwashed with aq NaHCO3, water, and brine
  9. dry with materialThe organic layer was dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-898c79f590c84e0aaf030c3829c1d13c
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

Loading…