Diisopropylethylamine → N-(5-cyano-2-methylphenyl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide

HRID 406817

反応式

HRID 406817 の反応式
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:9]([NH:17][C:18]3[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=1[CH3:36])[C:31]#[N:32].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O.C(OCC)(=O)C>[C:31]([C:30]1[CH:33]=[CH:34][C:35]([CH3:36])=[C:28]([NH:27][C:22](=[O:23])[C:21]2[CH:25]=[CH:26][C:18]([NH:17][C:9]3[N:8]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[N:10]=3)=[CH:19][CH:20]=2)[CH:29]=1)#[N:32]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 7764484-[(4-Phenylquinazolin-2-yl)amino]benzoic acidHCID 70164283-Amino-4-methylbenzonitrileHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 57662918N-(5-cyano-2-methylphenyl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide収率 65%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To a stirred mixture of 4-(4-phenylquinazolin-2-ylamino)benzoic acid (1.37 g, 4.02 mmol), 3-amino-4-methylbenzonitrile (529 mg, 4.01 mmol), and Hunig's base (2.1 mL, 12 mmol) in dimethylformamide (10 mL) was added HATU (3.04 g, 8.00 mmol). The stirred mixture was heated to 80° C. overnight, then cooled to rt. The reaction was diluted with ethyl acetate and extracted with water. The organic layer was washed with saturated sodium bicarbonate and concentrated on a rotary evaporator. The residue was sonicated with acetonitrile and filtered to give a light yellow solid, which was again washed with water, acetonitrile, and dried under reduced pressure to give N-(5-cyano-2-methylphenyl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide (1.18 g, 65%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 10.36 (s, 1H), 9.87 (s, 1H), 8.19 (d, 2H), 8.00 (d, 2H), 7.91-7.78 (m, 6H), 7.66-7.62 (m, 4H), 7.51 (d, 1H), 7.42 (ddd, 1H), 2.36 (s, 3H). MS (EI) for C29H21N5O: 456.1 (MH+).

後処理

  1. temperaturecooled to rt
  2. extractionextracted with water
  3. washThe organic layer was washed with saturated sodium bicarbonate
  4. concentrationconcentrated on a rotary evaporator
  5. customThe residue was sonicated with acetonitrile
  6. filtrationfiltered
  7. customto give a light yellow solid, which
  8. washwas again washed with water, acetonitrile
  9. customdried under reduced pressure

出典と根拠

ORDレコード
ord-f9982c41fce4408bb689202da5e135ad
出典データセット
uspto-grants-2014_06
特許番号
US08754092B2

関連ノート

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