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

HRID 908445Notes

Reaction equation

HRID 908445 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:36]([N:41]=1)=[N:37][CH:38]=[CH:39][CH:40]=2.[O:42]1[CH2:47][CH2:46][N:45]([CH2:48][CH2:49]O)[CH2:44][CH2:43]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=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:36]([N:41]=3)=[N:37][CH:38]=[CH:39][CH:40]=4)[C:18]([NH2:17])=[N:23][CH:22]=2)[CH:29]=[CH:28][C:27]=1[O:30][CH2:49][CH2:48][N:45]1[CH2:46][CH2:47][O:42][CH2:43][CH2:44]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 97268Di-tert-butyl azodicarboxylateHCID 673884864-(6-Amino-5-(oxazolo[4,5-b]pyridin-2-yl)pyridin-3-yl)-2-methoxyphenol

Product 1

HCID 673888645-[3-Methoxy-4-(2-morpholinoethoxy)phenyl]-3-oxazolo[4,5-b]pyridin-2-yl-pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

[C2] A solution of di-tert-butyl azodicarboxylate (241 mg) in dichloromethane (1 ml), was added dropwise to a stirred suspension of 4-(6-amino-5-(oxazolo[4,5-b]pyridin-2-yl)pyridin-3-yl)-2-methoxyphenol (130 mg), 2-morpholinoethanol (0.054 ml) and triphenylphosphine polymer bound (350 mg, 1.05 mmol) dissolved in dichloromethane (3 ml). The resulting suspension was stirred at room temperature for 2 hours. The mixture was filtered, washed with dichloromethane (1 ml) and methanol (1 ml). The solvent was evaporated. The resulting residue was diluted with 1 ml of dichloromethane and 1 ml of TFA; the mixture was stirred overnight and concentrated. The reaction mixture was purified by preparative HPLC using a Waters X-Bridge reverse-phase column (C-18, 5 microns silica, 19 mm diameter, 100 mm length, flow rate of 40 ml/minute) and decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. The fractions containing the desired compound were evaporated to dryness to afford 5-[3-methoxy-4-(2-morpholinoethoxy)phenyl]-3-oxazolo[4,5-b]pyridin-2-yl-pyridin-2-amine (70 mg) as a solid. The 4-(6-amino-5-oxazolo[4,5-b]pyridin-2-yl-3-pyridyl)-2-methoxy-phenol used as starting material was made as follows:

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with dichloromethane (1 ml) and methanol (1 ml)
  3. customThe solvent was evaporated
  4. additionThe resulting residue was diluted with 1 ml of dichloromethane and 1 ml of TFA
  5. stirringthe mixture was stirred overnight
  6. concentrationconcentrated
  7. customThe reaction mixture was purified by preparative HPLC
  8. additionThe fractions containing the desired compound
  9. customwere evaporated to dryness

Sources & evidence

ORD record
ord-640380ca69c74e9fb5390f98d98168b4
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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