Triphenylphosphine → 5-[3-Methoxy-4-(2-pyrrolidin-1-ylethoxy)phenyl]-3-oxazolo[5,4-b]pyridin-2-yl-pyridin-2-amine

HRID 908443노트

반응식

HRID 908443 반응식
N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.[NH2:17][C:18]1[N:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([O:31][CH3:32])[CH:25]=2)=[CH:20][C:19]=1[C:33]1[O:34][C:35]2[C:40]([N:41]=1)=[CH:39][CH:38]=[CH:37][N:36]=2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:61]1([CH2:66][CH2:67]O)[CH2:65][CH2:64][CH2:63][CH2:62]1>ClCCl>[CH3:32][O:31][C:26]1[CH:25]=[C:24]([C:21]2[CH:20]=[C:19]([C:33]3[O:34][C:35]4[C:40]([N:41]=3)=[CH:39][CH:38]=[CH:37][N:36]=4)[C:18]([NH2:17])=[N:23][CH:22]=2)[CH:29]=[CH:28][C:27]=1[O:30][CH2:67][CH2:66][N:61]1[CH2:65][CH2:64][CH2:63][CH2:62]1

참가 물질

6

반응물 4

HCID 11776Triphenylphosphine2회HCID 762881-PyrrolidineethanolHCID 97268Di-tert-butyl azodicarboxylateHCID 673886644-(6-Amino-5-oxazolo[5,4-b]pyridin-2-yl-3-pyridyl)-2-methoxy-phenol

생성물 1

HCID 673883945-[3-Methoxy-4-(2-pyrrolidin-1-ylethoxy)phenyl]-3-oxazolo[5,4-b]pyridin-2-yl-pyridin-2-amine수율 31%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

[C1] A solution of di-tert-butyl azodicarboxylate (37.9 mg) in dichloromethane (1 ml) was added to a stirred suspension of 4-(6-amino-5-(oxazolo[5,4-b]pyridin-2-yl)pyridin-3-yl)-2-methoxyphenol (50 mg), triphenylphosphine (43 mg) and 2-(pyrrolidin-1-yl)ethanol (19 mg) dissolved in dichloromethane (4 ml) under nitrogen. The resulting suspension was stirred at room temperature for 1 hour. Triphenylphosphine (43 mg) and a solution of DTAD (37.9 mg) in dichloromethane (1 ml) were added. The resulting mixture was stirred at room temperature for 20 minutes. After evaporation of the solvents, the residue was purified by flash chromatography on silica gel eluting with 5% methanol in dichloromethane and methanolic ammonia (7 N) in dichloromethane. After collection of the desired fractions and evaporation of the solvents, the resulting solid was triturated with acetonitrile to give 5-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)phenyl]-3-oxazolo[5,4-b]pyridin-2-yl-pyridin-2-amine (20 mg) as a solid. NMR Spectrum: (DMSOd6) 1.66-1.73 (m, 4H), 2.51-2.58 (m, 4H), 2.81 (t, 2H), 3.88 (s, 3H), 4.09 (t, 2H), 7.07 (d, 1H), 7.21 (dd, 1H), 7.28 (d, 1H), 7.53 (dd, 1H), 7.78 (bs, 2H), 8.30 (dd, 1H), 8.40 (dd, 1H), 8.47 (d, 1H), 8.60 (d, 1H)

후처리

  1. stirringThe resulting mixture was stirred at room temperature for 20 minutes
  2. customAfter evaporation of the solvents
  3. customthe residue was purified by flash chromatography on silica gel eluting with 5% methanol in dichloromethane and methanolic ammonia (7 N) in dichloromethane
  4. customAfter collection of the desired
  5. customfractions and evaporation of the solvents
  6. customthe resulting solid was triturated with acetonitrile

출처 및 근거

ORD 기록
ord-8cab270cfefd4f2b84fdd881f30a010f
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017611B2

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