Dimethylformamide dimethyl acetal → HCID 58980884, 화합물

HRID 1181339

반응식

HRID 1181339 반응식
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[S:4][C:3]=1[C:14]([O:16]C)=O.[CH3:18]OC(OC)N(C)C.[CH2:26]([O:28][CH:29]([O:41][CH2:42][CH3:43])[CH2:30][O:31][C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][C:33]=1[O:39][CH3:40])[CH3:27]>C(O)C>[Cl:13][C:10]1[CH:9]=[CH:8][C:7]([C:5]2[S:4][C:3]3[C:14](=[O:16])[N:36]([C:35]4[CH:37]=[CH:38][C:32]([O:31][CH2:30][CH:29]([O:28][CH2:26][CH3:27])[O:41][CH2:42][CH3:43])=[C:33]([O:39][CH3:40])[CH:34]=4)[CH:18]=[N:1][C:2]=3[CH:6]=2)=[CH:12][CH:11]=1

참가 물질

5

반응물 3

HCID 78373Dimethylformamide dimethyl acetalHCID 2777492Methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylateHCID 114367644-(2,2-Diethoxyethoxy)-3-methoxyaniline

생성물 1

HCID 58980884HCID 58980884, 화합물

시약·촉매·용매 1

HCID 702Ethanol용매2회

반응 조건

온도
90 °C

실험 절차

To a solution of methyl 3-amino-5-(4-chlorophenyl)-2-thiophenecarboxylate (2.0 g, 7.47 mmol, Maybridge, Inc) in ethanol (20 mL) was added dimethylformamide dimethyl acetal (2.5 mL, 2.5 eq, Aldrich). The reaction mixture was refluxed in a 90° C. oil bath for 3 h at which point the solvents were removed by rotary evaporation. Coevaporation with toluene removed the excess dimethylformamide dimethyl acetal. To the resulting residue was added ethanol (20 mL) and 4-(2,2-diethoxyethoxy)-3-methoxyaniline (2.3 g, 1.2 eq, Example H1). The reaction mixture was heated to 100° C. for 36 hours. The solvent was removed by rotary evaporation and the product purified by column chromatography followed by recrystallization from hot MeOH yielding the intermediate (0.82 g, 22%). 1H NMR (CDCl3) δ 1.22 (6H, t), 3.63-3.83 (4H, m), 3.90 (3H, s), 4.14 (2H, d, J=5.3 Hz), 4.92 (1H, t, J=5.2 Hz), 6.97 (2H), 7.06 (1H, d, J=8.5 Hz), 7.46 (2H, d, J=8.5 Hz), 7.58 (1H, s), 7.68 (2H, d, J=8.4 Hz), 8.24 (1H, br, s). LCMS m/z=501 (m+H+).

후처리

  1. customwere removed by rotary evaporation
  2. customCoevaporation with toluene removed the excess dimethylformamide dimethyl acetal
  3. temperatureThe reaction mixture was heated to 100° C. for 36 hours
  4. customThe solvent was removed by rotary evaporation
  5. customthe product purified by column chromatography
  6. customfollowed by recrystallization from hot MeOH yielding the intermediate (0.82 g, 22%)

출처 및 근거

ORD 기록
ord-5973a2071c764f3f86cac406276b2574
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07285557B2

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