Acetic Acid → HCID 89922683, 화합물

HRID 921849노트

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HRID 921849 반응식
[Cl:1][C:2]1[C:7]([CH:8]([CH3:11])[CH:9]=O)=[CH:6][C:5]([C:12]#[N:13])=[CH:4][C:3]=1[NH:14][C:15]1[N:20]=[C:19]([N:21]([CH:31]2[CH2:33][CH2:32]2)[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:18]2=[N:34][CH:35]=[C:36]([C:37]#[N:38])[N:17]2[N:16]=1.[NH:39]1[CH2:42][CH:41]([OH:43])[CH2:40]1.CC(O)=O.C([BH3-])#N.[Na+]>C1COCC1.CO.CCOC(C)=O>[Cl:1][C:2]1[C:7]([CH:8]([CH3:11])[CH2:9][N:39]2[CH2:42][CH:41]([OH:43])[CH2:40]2)=[CH:6][C:5]([C:12]#[N:13])=[CH:4][C:3]=1[NH:14][C:15]1[N:20]=[C:19]([N:21]([CH:31]2[CH2:33][CH2:32]2)[CH2:22][C:23]2[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)[C:18]2=[N:34][CH:35]=[C:36]([C:37]#[N:38])[N:17]2[N:16]=1

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 15142903-HydroxyazetidineHCID 5003444Sodium cyanoborohydrideHCID 89922524HCID 89922524, 화합물

생성물 1

HCID 89922683HCID 89922683, 화합물수율 63.7%

시약·촉매·용매 3

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

2-((2-chloro-5-cyano-3-(1-oxopropan-2-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (25 mg, 0.047 mmol) was taken up in THF (0.5 mL) and a solution of azetidin-3-ol (6.94 mg, 0.095 mmol) in MeOH (0.333 mL) was added. A drop of AcOH was added and the solution was stirred for 10 min. Next, sodium cyanoborohydride (5.96 mg, 0.095 mmol) was added and the reaction was stirred for 1 h. The reaction was diluted with EtOAc and washed with 2M K3PO4 solution. The organic layer was dried over Na2SO4, filtered, and concentrated. The material was purified by flash column chromatography (0-10% MeOHiDCM; 12 g column). 2-((2-chloro-5-cyano-3-(1-(3-hydroxyazetidin-1-yl)propan-2-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (17.5 mg) was obtained as a yellow glass.

후처리

  1. stirringthe reaction was stirred for 1 h
  2. washwashed with 2M K3PO4 solution
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe material was purified by flash column chromatography (0-10% MeOHiDCM; 12 g column)

출처 및 근거

ORD 기록
ord-e91af04dda534781924aade702c596f0
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273057B2

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