Ammonium Chloride → HCID 10622061, compound

HRID 1899888Notes

Reaction equation

HRID 1899888 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([S:8]([CH:11]2[S:15][C:14](=[O:16])[NH:13][C:12]2=[O:17])(=[O:10])=[O:9])[CH:5]=[CH:4][CH:3]=1.N1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1S(C1SC(=O)NC1=O)(=O)=O.FC1C=C(C#CCBr)C=C(F)C=1.[Cl-:50].[NH4+]>C1COCC1>[Cl:50][C:25]1[CH:26]=[CH:27][C:22]([C:21]#[C:20][CH2:19][C:11]2([S:8]([C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=3)(=[O:10])=[O:9])[S:15][C:14](=[O:16])[NH:13][C:12]2=[O:17])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 10492401HCID 10492401, compoundHCID 108286095-(Quinoline-2-sulfonyl)-thiazolidine-2,4-dioneHCID 19973049HCID 19973049, compound

Product 1

HCID 10622061HCID 10622061, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-butyl lithium (2.5 M in hexanes, 2.77 mL, 6.93 mmol) was added to a solution of 5-(6-methyl-pyridine-2-sulfonyl)-thiazolidine-2,4-dione, [(V), from Example 90, 0.92 g, 3.38 mmol] in dry THF (30 mL) at -78° C. under a dry N2 atmosphere over a twenty minute period. A solution of [3-(4-chlorophenyl)-prop-2ynyl]-bromide [(IX), from Example 21, 3.53 g, 15.4 mmol] in dry THF (10 mL) was added over a 20 rain period. The reaction mixture was allowed to warm to room temperature. After 16 h, the reaction mixture was added to saturated aqueous ammonium chloride (80 mL) and extracted with ethyl acetate (2×300 mL). The extracts were washed with water, dried (brine), concentrated and purified by flash chromatography (gradient 97:3 to 93:7 CH2Cl2 : isopropanol) to provide a sticky solid which triturated with petroleum ether (90 mL): benzene (2 mL) to provide the title compound as a off-white solid (0.55 g, 39%): mp 104°-106° C.: NMR (DMSO, d 6): δ 13.1 (broad s, 1H, N H), 8.10 (t, J=7.8 Hz, 1H, py H), 7.95 (d, J=7.7 Hz, 1H, py H), 7.71 (d, J=7.7 Hz, 1H, py H), 7.45 (d, J=8.8 Hz, 2H, Ar H), 7.35 (d, J=8.7 Hz, 2H, Ar H), 3.86 (d, J=17.4 Hz, 1H, C H2), 3.72 (d, J=17.4 Hz, 1H, C H2), 2.57 (s, 3H, C H3); MS(EI): 420 (MI, 3%), 265 (12%), 263 (38%), 194 (25%), 192 (70%), 149 (40%), 93 (100%); Anal. Calc. for C18H13ClN2O4S2 : C, 51.37; H, 3.11; N, 6.66; Found: C, 50.99; H, 3.05; N, 6.58.

Workup

  1. extractionextracted with ethyl acetate (2×300 mL)
  2. washThe extracts were washed with water
  3. dry with materialdried (brine)
  4. concentrationconcentrated
  5. custompurified by flash chromatography (gradient 97:3 to 93:7 CH2Cl2 : isopropanol)
  6. customto provide a sticky solid which
  7. customtriturated with petroleum ether (90 mL)

Sources & evidence

ORD record
ord-97d8ea213f1c4c90959c2e3fc2926f9c
Source dataset
uspto-grants-1996_11
Patent number
US05574051

Reaction notes

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