Benzaldehyde → 6-Amino-1-methyl-3,4-diphenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile

HRID 531182ノート

反応式

HRID 531182 の反応式
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9](#[N:13])[CH2:10][C:11]#[N:12].C(N(CC)CC)C.[CH3:21][N:22]1[C:26](=[O:27])[CH2:25][C:24]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[N:23]1>C(O)C>[NH2:12][C:11]1[O:27][C:26]2[N:22]([CH3:21])[N:23]=[C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:25]=2[CH:24]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:10]=1[C:9]#[N:13]

参加物

6

反応物 4

HCID 240BenzaldehydeHCID 8010MalononitrileHCID 8471TriethylamineHCID 1425623H-Pyrazol-3-one, 2,4-dihydro-2-methyl-5-phenyl-

生成物 1

HCID 896642926-Amino-1-methyl-3,4-diphenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile収率 299%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture consisting of benzaldehyde (290 μL, 2.87 mmol, 1.0 equ.), malononitrile (190 mg, 2.87 mmol, 1.0 equ.) and triethylamine (400 μL, 2.87 mmol, 1.0 equ.) in ethanol (10 mL) was stirred for 1 min, followed by the addition of 1-methyl-3-phenyl-1H-pyrazol-5(4H)-one (500 mg, 2.87 mmol, 1 equ.). The reaction mixture was concentrated after 21 h and washed with ethanol and hexanes; re-crystallized from ethanol, and washed with hexanes and ethanol to give 6-amino-1-methyl-3,4-diphenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile (282 mg, 8.58 mmol, 30%) as a white solid. 1H-NMR (400 MHz) DMSO: 7.41-7.38 (m, 2H), 7.28-7.24 (m, 2H), 7.21-7.18 (m, 6H), 4.88 (s, 1H), 4.77 (s, 2 H), 3.83 (s, 3H), 13C-NMR (100 MHz) DMSO: 158.1, 146.0, 144.8, 144.6, 133.2, 128.7, 128.5, 127.9, 127.8, 127.1, 126.4, 120.5, 95.7, 59.9, 38.2, 34.5; LC/MS-MS: 329.1-263.1 m/z; GS1 and GS2 at 30, DP=71, CE=31, CXP=18, tR=4.00 min.

後処理

  1. concentrationThe reaction mixture was concentrated after 21 h
  2. washwashed with ethanol and hexanes
  3. customre-crystallized from ethanol
  4. washwashed with hexanes and ethanol

出典と根拠

ORDレコード
ord-43ccf3c0b16a4e0e9a5aa9db7acc9428
出典データセット
uspto-grants-2016_05
特許番号
US09353121B2

反応ノート

読み込み中…