Ammonium Chloride → HCID 10622061、化合物

HRID 1451828ノート

反応式

HRID 1451828 の反応式
[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.F[C:19]1[CH:20]=[C:21]([C:26]#[C:27][CH2:28]Br)[CH:22]=[C:23](F)[CH:24]=1.[Cl-:30].[NH4+]>C1COCC1>[Cl:30][C:24]1[CH:23]=[CH:22][C:21]([C:26]#[C:27][CH2:28][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:20][CH:19]=1

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 10492401HCID 10492401、化合物2 回HCID 19973049HCID 19973049、化合物

生成物 1

HCID 10622061HCID 10622061、化合物収率 39%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

N-butyl lithium (2.5M 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-2-ynyl]-BROMIDE [(IX), from Example 21, 3.53 g, 15.4 mmol] in dry THF (10 mL) was added over a 20 min 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): δ13.1 (broad s, 1H, NH), 8.10 (t, J=7.8 Hz, 1H, pyH), 7.95 (d, J=7.7 Hz, 1H, pyH), 7.71 (d, J=7.7 Hz, 1H, pyH), 7.45 (d, J=8.8 Hz, 2H, ArH), 7.35 (d, J=8.7 Hz, 2H, ArH), 3.86 (d, J=17.4 Hz, 1H, CH2), 3.72 (d, J=17.4 Hz, 1H, CH2), 2.57 (s, 3H, CH3); 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.

後処理

  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)

出典と根拠

ORDレコード
ord-74d359c09dcb401b9686138291e267ba
出典データセット
uspto-grants-1997_02
特許番号
US05605918

反応ノート

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