Pyridine → HCID 10050552, compound

HRID 2293922Notes

Reaction equation

HRID 2293922 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH3:11])=[C:4]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([I:20])[CH:15]=2)[N:3]=1.O.[SH-:22].[Na+].[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[I:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[CH2:13][NH:12][C:4]1[N:3]=[C:2]([S:22][C:27]2[CH:28]=[CH:29][N:24]=[CH:25][CH:26]=2)[N:10]=[C:9]2[C:5]=1[N:6]=[CH:7][N:8]2[CH3:11]

Participants

4

Reactant 3

HCID 1049PyridineHCID 10340909HCID 10340909, compoundHCID 16211346Sodium hydrosulfide hydrate

Product 1

HCID 10050552HCID 10050552, compoundYield 27.4%

Conditions

Temperature
100 °C

Procedure

A mixture of compound 6 (20.4 mg, 0.051 mmol) and sodium hydrosulfide hydrate (11 mg, 0.2 mmol) in pyridine (1.5 mL) was heated for 5 days at 100° C. After cooling, the reaction mixture was concentrated to dryness and the residue was purified on preparative TLC (chloroform-methanol, 20:1) to give compound 17 (6.5 mg, 27.4%) as a yellow solid. 1H NMR (DMSO-d6) δ 3.78 (s, 3 H, CH3), 4.70 (br s, 2 H, CH2), 7.13 (pseudo t, J=7.6 and 7.5 Hz, 1 H, H-16), 7.29 (d, J=7.2 Hz, 2 H, pyr), 7.45 (d, J=7.2 Hz, 1 H, H-17), 7.60 (d, J=8.2 Hz, 1 H, H-15), 7.86 (s, 1 H, H-13), 8.22 (s, 1 H, H-8), 8.73 (d, J=7.2 Hz, 2 H, pyr), 9.03 (br s, 1 H, exchangeable with D2O, NH).

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated to dryness
  3. customthe residue was purified on preparative TLC (chloroform-methanol, 20:1)

Sources & evidence

ORD record
ord-085ee58885a641419c40fc1f11ad6393
Source dataset
uspto-grants-1997_11
Patent number
US05688774

Reaction notes

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