Formamide → 1-(4-methoxyphenyl)-6-(4-{2-[(methylamino)methyl]phenyl}phenyl)-7-oxo-1H,4H,5H,6H,7H-pyrazolo[3,4-c]pyridine-3-carboxamide

HRID 860834ノート

反応式

HRID 860834 の反応式
C([O:3][C:4]([C:6]1[C:14]2[CH2:13][CH2:12][N:11]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH2:27][NH:28][CH3:29])=[CH:17][CH:16]=3)[C:10](=[O:30])[C:9]=2[N:8]([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)[N:7]=1)=O)C.C([NH2:41])=O.CO[Na].O>CN(C=O)C.CO>[CH3:38][O:37][C:34]1[CH:35]=[CH:36][C:31]([N:8]2[C:9]3[C:10](=[O:30])[N:11]([C:15]4[CH:20]=[CH:19][C:18]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=5[CH2:27][NH:28][CH3:29])=[CH:17][CH:16]=4)[CH2:12][CH2:13][C:14]=3[C:6]([C:4]([NH2:41])=[O:3])=[N:7]2)=[CH:32][CH:33]=1

参加物

7

反応物 4

HCID 713FormamideHCID 962WaterHCID 223185241-(4-Methoxy-phenyl)-6-(2'-methylaminomethyl-biphenyl-4-yl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c)pyridine-3-carboxylic acid ethyl esterHCID 178418582HCID 178418582、化合物

生成物 1

HCID 101167521-(4-methoxyphenyl)-6-(4-{2-[(methylamino)methyl]phenyl}phenyl)-7-oxo-1H,4H,5H,6H,7H-pyrazolo[3,4-c]pyridine-3-carboxamide収率 83%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of 1-(4-methoxy-phenyl)-6-(2′-methylaminomethyl-biphenyl-4-yl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester (57, 13.5 g, 26.4 mmol) in DMF (50 mL) was treated with formamide (8.32 g, 6.2 mL, 184.8 mmol, 7.0 equiv) at room temperature, and the resulting reaction mixture was cooled down to 0–5° C. before being treated dropwise with a solution of MeONa (8.6 g, 9.05 mL, 39.6 mmol, 1.5 equiv) in methanol at 0–5° C. The resulting reaction mixture was stirred at 0–5° C. for 30 min before being gradually warmed up to room temperature for an additional 3 h. When HPLC and TLC showed the reaction was complete, the reaction mixture was slowly poured into water (600 mL). The resulting mixture was then stirred at room temperature for 1 h to precipitate the desired product. The solids were collected by filtration, washed with water (2×100 mL) and methyl tert-butyl ether (2×100 mL), dried in vacuo at 40–45° C. for 12 h to afford crude desired 1-(4-methoxy-phenyl)-6-(2′-methylaminomethyl-biphenyl-4-yl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid amide (58, 10.55 g, 12.71 g theoretical, 83%). This crude solids were subsequently recrystallized in a mixture of ethanol and methanol to afford the pure product. For 58, CIMS m/z 482 (M++H, C28H27N5O3).

後処理

  1. customthe resulting reaction mixture
  2. temperaturewas cooled down to 0–5° C.
  3. customThe resulting reaction mixture
  4. stirringThe resulting mixture was then stirred at room temperature for 1 h
  5. customto precipitate the desired product
  6. filtrationThe solids were collected by filtration
  7. washwashed with water (2×100 mL) and methyl tert-butyl ether (2×100 mL)
  8. customdried in vacuo at 40–45° C. for 12 h

出典と根拠

ORDレコード
ord-1e4942799f2b4303aed7f2b533055d1f
出典データセット
uspto-grants-2006_12
特許番号
US07153960B2

反応ノート

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