Ammonium Chloride → HCID 10622061, 화합물

HRID 1451828노트

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HRID 1451828 반응식
[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

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 10492401HCID 10492401, 화합물2회HCID 19973049HCID 19973049, 화합물

생성물 1

HCID 10622061HCID 10622061, 화합물수율 39%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-74d359c09dcb401b9686138291e267ba
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05605918

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