Potassium Carbonate → 7-[3-(1,1-Dioxido-1,2-thiazolidin-2-yl)phenyl]-2-(methylsulfanyl)pyrrolo[2,1-f][1,2,4]triazine

HRID 1262410ノート

反応式

HRID 1262410 の反応式
[CH3:1][S:2][C:3]1[N:8]=[CH:7][C:6]2=[CH:9][CH:10]=[C:11]([C:12]3[CH:13]=[C:14]([NH2:18])[CH:15]=[CH:16][CH:17]=3)[N:5]2[N:4]=1.C(N(CC)C(C)C)(C)C.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:35][CH2:36][CH2:37][S:38](Cl)(=[O:40])=[O:39]>CN(C)C=O.CCOC(C)=O.O>[O:39]=[S:38]1(=[O:40])[CH2:37][CH2:36][CH2:35][N:18]1[C:14]1[CH:13]=[C:12]([C:11]2[N:5]3[C:6]([CH:7]=[N:8][C:3]([S:2][CH3:1])=[N:4]3)=[CH:9][CH:10]=2)[CH:17]=[CH:16][CH:15]=1

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 154103-Chloropropanesulphonyl chloride2 回HCID 81531Diisopropylethylamine2 回HCID 667126823-(2-Methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenylamine

生成物 1

HCID 667117407-[3-(1,1-Dioxido-1,2-thiazolidin-2-yl)phenyl]-2-(methylsulfanyl)pyrrolo[2,1-f][1,2,4]triazine収率 46.5%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

3-(2-Methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenylamine (0.795 g, 3.10 mmol) was dissolved in N,N-Dimethylformamide (12.0 mL) and N,N-Diisopropylethylamine (1.50 mL, 8.61 mmol). Potassium carbonate (1.28 g, 9.30 mmol) was added, followed by 3-Chloropropane-1-sulfonyl chloride (0.450 mL, 3.70 mmol) and stirred overnight. After 24 h, a second aliquot of N,N-Diisopropylethylamine (2.00 mL, 11.5 mmol) and 3-Chloropropane-1-sulfonyl chloride (0.50 mL, 4.1 mmol) was added and stirred additionally. When conversion had reached ca. 90%, the mixture was treated with water (40 mL) and EtOAc (40 mL). The layers were separated, the aq. extr. with EtOAc (3×20 mL) and the comb. org. diluted with hexane (20 mL) and washed with water (30 ml) and brine (30 mL). After drying over sodium sulfate, the mixture was filtered and conc. in vacuo and applied to a 25 g ISCO loading cartridge. Purification on ISCO (40 g column, 10-70% EtOAc:Hex) afforded 7-[3-(1,1-Dioxido-1,2-thiazolidin-2-yl)phenyl]-2-(methylsulfanyl)pyrrolo[2,1-f][1,2,4]triazine (0.52 g; Yield=46%) as a yellow solid. 1H-NMR (CDCl3): 8.74 (s, 1H), 8.06 (s, 1H), 7.86 (d, 1H, J=7.9 Hz), 7.47 (m, 1H), 7.28 (m, 1H), 7.27 (s, 1H), 7.12 (d, 1H, J=4.8 Hz), 6.89 (d, 1H, J=4.8 Hz), 3.86 (t, 2H, J=6.5 Hz), 3.42 (t, 2H, J=7.4 Hz), 2.62 (s, 3H), 2.58 (m, 2H).

後処理

  1. waitAfter 24 h
  2. stirringstirred additionally
  3. customThe layers were separated
  4. additiondiluted with hexane (20 mL)
  5. washwashed with water (30 ml) and brine (30 mL)
  6. dry with materialAfter drying over sodium sulfate
  7. filtrationthe mixture was filtered and conc. in vacuo
  8. customPurification on ISCO (40 g column, 10-70% EtOAc:Hex)

出典と根拠

ORDレコード
ord-efe2dbe425ee4d9d9349e5f0f34b9030
出典データセット
uspto-grants-2013_06
特許番号
US08471005B2

反応ノート

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