Citric Acid → 4-[4-(4-Bromoindol-1-yl)-pyrimidin-2-ylamino]-cyclo-hexanecarboxylic acid

HRID 1516442노트

반응식

HRID 1516442 반응식
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]2[N:18]=[C:17]([N:19]3[C:27]4[C:22](=[C:23]([Br:28])[CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:20]3)[CH:16]=[CH:15][N:14]=2)[CH2:8][CH2:7]1)=[O:5])C.O[Li].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CCO.O>[Br:28][C:23]1[CH:24]=[CH:25][CH:26]=[C:27]2[C:22]=1[CH:21]=[CH:20][N:19]2[C:17]1[CH:16]=[CH:15][N:14]=[C:13]([NH:12][CH:9]2[CH2:8][CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]2)[N:18]=1

참가 물질

7

반응물 3

HCID 311Citric AcidHCID 168937Lithium hydroxide, monohydrateHCID 686055994-[4-(4-Bromoindol-1-yl)-pyrimidin-2-ylamino]-cyclohexanecarboxylic acid ethyl ester

생성물 1

HCID 674356194-[4-(4-Bromoindol-1-yl)-pyrimidin-2-ylamino]-cyclo-hexanecarboxylic acid수율 97%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 4-[4-(4-bromoindol-1-yl)-pyrimidin-2-ylamino]-cyclohexane-carboxylic acid ethyl ester (5.8 g) and LiOH.H2O (1.65 g) in THF (100 mL), EtOH (40 mL) and H2O (30 mL) was stirred at RT overnight. The reaction mixture was then acidified with citric acid (7.54 g in 20 mL H2O), and stirred at RT for 1 h. The precipitate was filtered, washed with water, then Et2O, and dried to provide 4-[4-(4-bromoindol-1-yl)-pyrimidin-2-ylamino]-cyclo-hexanecarboxylic acid (5.27 g, 97%) as a white powder.

후처리

  1. stirringstirred at RT for 1 h
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. dry with materialEt2O, and dried

출처 및 근거

ORD 기록
ord-67f8480cacb843d6971463a77acdfadd
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08227478B2

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