Acetic Acid → 8-[(1-acetylpiperidin-4-yl)amino]-N-(2,6-diethylphenyl)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

HRID 81953

反応式

HRID 81953 の反応式
Cl.[CH2:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH3:11])[C:5]=1[NH:12][C:13]([C:15]1[C:19]2[CH2:20][CH2:21][C:22]3[CH:23]=[N:24][C:25]([NH:28][CH:29]4[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]4)=[N:26][C:27]=3[C:18]=2[N:17]([CH3:35])[N:16]=1)=[O:14])[CH3:3].CCN(C(C)C)C(C)C.ON1C2C=CC=CC=2N=N1.[C:55](O)(=[O:57])[CH3:56]>CN(C)C=O.O>[C:55]([N:32]1[CH2:31][CH2:30][CH:29]([NH:28][C:25]2[N:24]=[CH:23][C:22]3[CH2:21][CH2:20][C:19]4[C:15]([C:13]([NH:12][C:5]5[C:4]([CH2:2][CH3:3])=[CH:9][CH:8]=[CH:7][C:6]=5[CH2:10][CH3:11])=[O:14])=[N:16][N:17]([CH3:35])[C:18]=4[C:27]=3[N:26]=2)[CH2:34][CH2:33]1)(=[O:57])[CH3:56]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 44555920N-(2,6-diethylphenyl)-1-methyl-8-(piperidin-4-ylamino)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide hydrochloride

生成物 1

HCID 445559698-[(1-acetylpiperidin-4-yl)amino]-N-(2,6-diethylphenyl)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide収率 77%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of N-(2,6-diethylphenyl)-1-methyl-8-(piperidin-4-ylamino)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide hydrochloride (40 mg, 0.075 mmol) in dimethylformamide (1 mL), DIPEA (0.2 mL, 1.1 mmol), N-ethyl-N′,N′-diisopropyl carbodiimide hydrochloride (EDCI) (22 mg, 0.113 mmol), 1-hydroxy-benzotriazole (18 mg, 0.113 mmol) and acetic acid (0.005 mL, 0.009 mmol) were added. The mixture was stirred at room temperature for 6 h. Water was added and the mixture extracted with ethylacetate. The organic layer was washed with brine then dried over Na2SO4 and the solvent evaporated to dryness. The crude solid was purified by flash chromatography on silica gel (eluant: dichloromethane/methanol: 97/3) to 29 mg of the title compound. (77% yield)

後処理

  1. extractionthe mixture extracted with ethylacetate
  2. washThe organic layer was washed with brine
  3. dry with materialthen dried over Na2SO4
  4. customthe solvent evaporated to dryness
  5. customThe crude solid was purified by flash chromatography on silica gel (eluant: dichloromethane/methanol: 97/3) to 29 mg of the title compound

出典と根拠

ORDレコード
ord-d05b63ba905e4fbd9ac1a9de6257d37b
出典データセット
uspto-grants-2014_09
特許番号
US08846701B2

関連ノート

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