Potassium Carbonate → Methyl 2-(6-chloro-4-(isopropylamino)pyridin-3-yl)-4,5-dihydrooxazole-4-carboxylate

HRID 595494Notes

Reaction equation

HRID 595494 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([NH:18][CH:19]([CH3:21])[CH3:20])[C:5]([C:6]([NH:8][CH:9]([CH2:14][OH:15])[C:10]([O:12][CH3:13])=[O:11])=O)=[CH:4][N:3]=1.CCN(S(F)(F)F)CC.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:6]2[O:15][CH2:14][CH:9]([C:10]([O:12][CH3:13])=[O:11])[N:8]=2)=[C:16]([NH:18][CH:19]([CH3:21])[CH3:20])[CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123472(Diethylamino)sulfur trifluorideHCID 89689704Methyl 2-(6-chloro-4-(isopropylamino)nicotinamido)-3-hydroxypropanoate

Product 1

HCID 89689795Methyl 2-(6-chloro-4-(isopropylamino)pyridin-3-yl)-4,5-dihydrooxazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of methyl 2-(6-chloro-4-(isopropylamino)nicotinamido)-3-hydroxypropanoate (36) (100 mg, 0.317 mmol) in DCM (15 mL), DAST (0.317 mmol) was added at −78° C. and stirred for 4 h. K2CO3 (0.633 mmol) was added to the reaction mixture and stirred for 3 h. The reaction mixture was diluted with DCM and washed with water (twice) followed by brine solution. The organic layer was collected, dried over Na2SO4, filtered and concentrated. The crude material obtained was purified by flash chromatography using silica gel and EtOAC:pet ether as eluent to afford the title compound, methyl 2-(6-chloro-4-(isopropylamino)pyridin-3-yl)-4,5-dihydrooxazole-4-carboxylate. 1H NMR: 400 MHz, DMSO-d6: δ 1.20-1.21 (m, 6H), 3.73 (s, 3H), 3.84-3.89 (m, 1H), 4.51-4.59 (m, 2H), 5.07-5.12 (m, 1H), 6.83 (s, 1H), 8.36 (s, 1H), 8.80 (d, J=7.60 Hz, 1H).

Workup

  1. stirringstirred for 3 h
  2. washwashed with water (twice)
  3. customThe organic layer was collected
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material obtained
  8. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-3d7330ff49cd4dc9bc1325429be71c81
Source dataset
uspto-grants-2016_01
Patent number
US09242976B2

Reaction notes

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