Triphenylphosphine → 5-methyl-3-{3-[5-(4-methylpiperazin-1-yl)pyrimidin-2-yl]benzyl}-3H-oxazolo[4,5-b]pyridin-2-one

HRID 1970884노트

반응식

HRID 1970884 반응식
[CH3:1][C:2]1[N:7]=[C:6]2[NH:8][C:9](=[O:11])[O:10][C:5]2=[CH:4][CH:3]=1.[CH3:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:20]=[N:21][C:22]([C:25]3[CH:26]=[C:27]([CH2:31]O)[CH:28]=[CH:29][CH:30]=3)=[N:23][CH:24]=2)[CH2:15][CH2:14]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>CN(C=O)C>[CH3:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:31][C:27]3[CH:28]=[CH:29][CH:30]=[C:25]([C:22]4[N:23]=[CH:24][C:19]([N:16]5[CH2:15][CH2:14][N:13]([CH3:12])[CH2:18][CH2:17]5)=[CH:20][N:21]=4)[CH:26]=3)[C:9](=[O:11])[O:10][C:5]2=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 100120755-Methyloxazolo[4,5-b]pyridin-2(3H)-oneHCID 59484860{3-[5-(4-Methylpiperazin-1-yl)pyrimidin-2-yl]phenyl}methanol

생성물 1

HCID 584861045-methyl-3-{3-[5-(4-methylpiperazin-1-yl)pyrimidin-2-yl]benzyl}-3H-oxazolo[4,5-b]pyridin-2-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

67 mg (0.44 mmol) of 5-methyl-3H-oxazolo[4,5-b]pyridin-2-one and 125 mg (0.44 mmol) of {3-[5-(4-methylpiperazin-1-yl)pyrimidin-2-yl]phenyl}methanol are suspended in 5 ml of DMF with 222 mg (0.67 mmol) of polymer-bound triphenylphosphine (about 3 mmol of triphenylphosphine per g), and the mixture is shaken at room temperature for 30 min. 156 mg (0.67 mmol) of di-tert-butyl azodicarboxylate are added. The reaction mixture is shaken at room temperature for 15 h. The reaction mixture is filtered, the residue is evaporated, and the residue is purified by column chromatography on silica gel, giving 67 mg of “A125”; HPLC: Rt=2.20 min (method B); ESI: 418 (M+H);

후처리

  1. stirringThe reaction mixture is shaken at room temperature for 15 h
  2. filtrationThe reaction mixture is filtered
  3. customthe residue is evaporated
  4. customthe residue is purified by column chromatography on silica gel
  5. customgiving 67 mg of “A125”

출처 및 근거

ORD 기록
ord-ac234d0ada944ff1a67316ad3eeb55a8
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431572B2

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