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 1867683노트

반응식

HRID 1867683 반응식
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]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 57979867HCID 57979867, 화합물

생성물 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

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b62e641a614149b19b739e3c28282ceb
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07632840B2

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