Potassium Carbonate → HCID 136009420, compound

HRID 1969901Notes

Reaction equation

HRID 1969901 reaction equation
[CH2:1]([C@H:3]1[C@@H:7]([C:8]2[N:12]3[C:13]4[CH:19]=[CH:18][NH:17][C:14]=4[N:15]=[CH:16][C:11]3=[N:10][N:9]=2)[CH2:6][C@@H:5]([CH2:20][C:21](OCC)=[O:22])[CH2:4]1)[CH3:2].O/[N:27]=[C:28](\[NH2:32])/[CH2:29][O:30][CH3:31].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.CO>[CH2:1]([C@H:3]1[C@@H:7]([C:8]2[N:12]3[C:13]4[CH:19]=[CH:18][NH:17][C:14]=4[N:15]=[CH:16][C:11]3=[N:10][N:9]=2)[CH2:6][C@@H:5]([CH2:20][C:21]2[O:22][N:32]=[C:28]([CH2:29][O:30][CH3:31])[N:27]=2)[CH2:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 652229195298-88-7HCID 136009208HCID 136009208, compound

Product 1

HCID 136009420HCID 136009420, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of ethyl 2-((1S,3R,4S)-3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)acetate (0.100 g, 0.293 mmol) in toluene (0.20 mL) and MeOH (0.20 mL) was added (Z)-N′-hydroxy-2-methoxyacetimidamide (0.300 g, 2.89 mmol, Tyger) and K2CO3 (0.100 g, 0.726 mmol). The solution was heated in a CEM microwave at about 130° C. for about 1 h (250 psi maximum pressure, 1 min ramp, 300 max watts). The solvent was removed under reduced pressure. The residue was diluted with DCM (3 mL) and a small amount of MeOH. The crude material was purified by flash chromatography on silica gel eluting with a gradient of 0-10% MeOH in DCM. The residue was dissolved in EtOAc and heptane was added. The solvent was concd. The solid was dried in a heated vacuum oven (about 70° C.) for about 20 h to afford 5-(((1S,3R,4S)-3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)methyl)-3-(methoxymethyl)-1,2,4-oxadiazole (0.062 g, 56%) as a white solid: LC/MS (Table 1, Method a) Rt=1.79 min; MS m/z: 382 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was diluted with DCM (3 mL)
  3. customThe crude material was purified by flash chromatography on silica gel eluting with a gradient of 0-10% MeOH in DCM
  4. dissolutionThe residue was dissolved in EtOAc
  5. additionheptane was added
  6. customThe solid was dried in a heated vacuum oven (about 70° C.) for about 20 h

Sources & evidence

ORD record
ord-15ae2537515c4d1385e7b4bcb6af65f6
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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