Ammonium Chloride → HCID 10622061、化合物

HRID 1899888ノート

反応式

HRID 1899888 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.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

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 10492401HCID 10492401、化合物HCID 108286095-(Quinoline-2-sulfonyl)-thiazolidine-2,4-dioneHCID 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 (2.5 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.

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-97d8ea213f1c4c90959c2e3fc2926f9c
出典データセット
uspto-grants-1996_11
特許番号
US05574051

反応ノート

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