Thiourea → HCID 178451223、化合物

HRID 2389463ノート

反応式

HRID 2389463 の反応式
Cl[C:2]1[N:6]([CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N:3]=1.NC(N)=[S:21]>CO>[C:11]([O:10][C:8](=[O:9])[CH2:7][N:6]1[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N:3]=[C:2]1[SH:21])([CH3:14])([CH3:13])[CH3:12]

参加物

4

反応物 2

HCID 2723790ThioureaHCID 86224963tert-Butyl (2-chloro-benzoimidazol-1-yl)-acetate

生成物 1

HCID 178451223HCID 178451223、化合物収率 92.9%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

According to the procedure described in: Migawa, M. T.; Girardet, J.-L.; Walker II, J. A.; Koszalka, G. W.; Chamberlain, S. D.; Drach, J. C.; Townsend, L. B., J. Med. Chem. 1998, 41, 1242-1251, a solution of tert-butyl (2-chloro-benzoimidazol-1-yl)-acetate (Intermediate 2-I, 7 g, 26.3 mmol) and thiourea (7.98 g, 105 mmol) in methanol (100 ml) is refluxed for 2 h. The mixture is cooled down and most of the methanol is removed in vacuo. After addition of saturated aqueous NH4Cl solution (150 ml), the resulting aqueous phase is extracted three times with Et2O. The combined organic phases are washed with brine and dried over Na2SO4. The solvent is evaporated in vacuo and the residue dried under high vacuum, yielding the title compound (6.46 g) in 93% as a white powder: tR=6.14 min (LC-1), ESI-MS (neg.): m/z 263.31 [M−H]+; 1H-NMR (CDCl3): δ (ppm) 1.50 (s, 9H, tBu), 4.94 (s, 2H, CH2CO2), 6.99-7.05 (m, 1 Harom), 7.16-7.24 (m, 1Harom), 10.69 (bs, 1H, SH).

後処理

  1. customis removed in vacuo
  2. additionAfter addition of saturated aqueous NH4Cl solution (150 ml)
  3. extractionthe resulting aqueous phase is extracted three times with Et2O
  4. washThe combined organic phases are washed with brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent is evaporated in vacuo
  7. customthe residue dried under high vacuum

出典と根拠

ORDレコード
ord-aacda600cbb84607942fb46c6aa58064
出典データセット
uspto-grants-2012_09
特許番号
US08273740B2

反応ノート

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