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

HRID 908443Notes

Reaction equation

HRID 908443 reaction equation
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

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 762881-PyrrolidineethanolHCID 97268Di-tert-butyl azodicarboxylateHCID 673886644-(6-Amino-5-oxazolo[5,4-b]pyridin-2-yl-3-pyridyl)-2-methoxy-phenol

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

[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)

Workup

  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

Sources & evidence

ORD record
ord-8cab270cfefd4f2b84fdd881f30a010f
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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