Triethylamine → 2-{4-(Aminocarbonyl)-4-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]piperidin-1-yl}-2-oxoethyl acetate

HRID 1867683ノート

反応式

HRID 1867683 の反応式
C(N(CC)CC)C.[Cl:8][C:9]1[C:10]([F:40])=[C:11]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][C:22]([O:38][CH3:39])=[C:23]([CH2:26][N:27]([CH3:37])[C:28]4([C:34]([NH2:36])=[O:35])[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]4)[CH:24]=3)[N:19]=[CH:18][N:17]=2)[CH:12]=[CH:13][CH:14]=1.[C:41]([O:44][CH2:45][C:46](Cl)=[O:47])(=[O:43])[CH3:42]>CN1C(=O)CCC1>[C:41]([O:44][CH2:45][C:46]([N:31]1[CH2:32][CH2:33][C:28]([C:34]([NH2:36])=[O:35])([N:27]([CH2:26][C:23]2[CH:24]=[C:25]3[C:20](=[CH:21][C:22]=2[O:38][CH3:39])[N:19]=[CH:18][N:17]=[C:16]3[NH:15][C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([Cl:8])[C:10]=2[F:40])[CH3:37])[CH2:29][CH2:30]1)=[O:47])(=[O:43])[CH3:42]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 57979867HCID 57979867、化合物

生成物 1

HCID 690489122-{4-(Aminocarbonyl)-4-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]piperidin-1-yl}-2-oxoethyl acetate

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

Triethylamine (360 μl, 2.58 mmol) was added to a stirred, cooled (0° C.) suspension of 4-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]piperidine-4-carboxamide (300 mg, 0.63 mmol) (Example 16) in NMP (5 ml). Acetoxyacetyl chloride (100 μl 0.93 mmol) was then added drop wise and the reaction mixture left to warm to room temperature over a period of 2 hours. This was then partitioned between saturated aqueous sodium hydrogen carbonate solution and ethyl acetate. The organic phase was washed with saturated aqueous ammonium chloride solution followed by brine, dried over magnesium sulfate, filtered and evaporated to give 2-{4-(aminocarbonyl)-4-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]piperidin-1-yl}-2-oxoethyl acetate as a dry film (250 mg). Mass spectrum: (M+H)+ 573.

後処理

  1. temperaturecooled
  2. waitthe reaction mixture left
  3. customThis was then partitioned between saturated aqueous sodium hydrogen carbonate solution and ethyl acetate
  4. washThe organic phase was washed with saturated aqueous ammonium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

出典と根拠

ORDレコード
ord-b62e641a614149b19b739e3c28282ceb
出典データセット
uspto-grants-2009_12
特許番号
US07632840B2

反応ノート

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