5-methyl-1H-pyrazole-3-carboxylic acid → 1-isopropyl-6-(5-methyl-1H-pyrazol-3-yl)-3,5-dihydro-1H-benzo[1,2-d;4,5-d']diimidazol-2-one

HRID 1181580

反応式

HRID 1181580 の反応式
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([C:7](O)=O)[CH:3]=1.[NH2:10][C:11]1[C:23]([NH2:24])=[CH:22][C:14]2[N:15]([CH:19]([CH3:21])[CH3:20])[C:16](=[O:18])[NH:17][C:13]=2[CH:12]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>>[CH:19]([N:15]1[C:14]2[CH:22]=[C:23]3[C:11](=[CH:12][C:13]=2[NH:17][C:16]1=[O:18])[NH:10][C:7]([C:4]1[CH:3]=[C:2]([CH3:1])[NH:6][N:5]=1)=[N:24]3)([CH3:21])[CH3:20]

参加物

4

反応物 3

HCID 98225-methyl-1H-pyrazole-3-carboxylic acidHCID 14812Phosphorus oxide (P4O10)HCID 695075865,6-Diamino-1-isopropyl-1,3-dihydro-benzoimidazol-2-one

生成物 1

HCID 1354758681-isopropyl-6-(5-methyl-1H-pyrazol-3-yl)-3,5-dihydro-1H-benzo[1,2-d;4,5-d']diimidazol-2-one

実験手順

5-Methyl-1H-pyrazole-3-carboxylic acid (126 mg, 1 mmol) and 5,6-diamino-1-isopropyl-1,3-dihydro-benzoimidazol-2-one (206 mg, 1 mmol) were heated to 160° C. in a mixture of polyphosphoric acid (5 g) and phosphorus pentoxide (500 mg, 3.5 mmol) for 6 h. This mixture was poured on water (20 ml) and stirring continued until a precipitate formed. After filtration the crude product was suspended in water and neutralized by the addition of aqueous ammonia (25%). The precipitate was collected, washed with water and dried in vacuo. Purification was achieved by chromatography on silica (dichloromethane/methanol 95:5) yielding 1-isopropyl-6-(5-methyl-1H-pyrazol-3-yl)-3,5-dihydro-1H-benzo[1,2-d;4,5-d′]diimidazol-2-one as slightly yellow solid. Yield 36 mg (12%)

後処理

  1. additionThis mixture was poured on water (20 ml)
  2. customformed
  3. filtrationAfter filtration the crude product
  4. additionneutralized by the addition of aqueous ammonia (25%)
  5. customThe precipitate was collected
  6. washwashed with water
  7. customdried in vacuo
  8. customPurification

出典と根拠

ORDレコード
ord-2d16a06f3e9e4b2b9c3c4588f9fa6122
出典データセット
uspto-grants-2007_10
特許番号
US07285569B2

関連ノート

読み込み中…