2-Pyrazinecarboxylic acid → HCID 58758434, compound

HRID 459043Notes

Reaction equation

HRID 459043 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([OH:9])=[O:8].[F:10][C:11]1[CH:12]=[C:13]([N:30]2[CH2:34][C@H:33]([CH2:35][N:36]3[CH:40]=[CH:39][N:38]=[N:37]3)[O:32][C:31]2=[O:41])[CH:14]=[CH:15][C:16]=1[C:17]1[CH:18]=[N:19][C:20]([C:23]2[CH2:27][C@@H:26]([CH2:28]O)[O:25][N:24]=2)=[CH:21][CH:22]=1.CN(C=O)C.C(N=C=NC(C)C)(C)C>CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[F:10][C:11]1[CH:12]=[C:13]([N:30]2[CH2:34][C@H:33]([CH2:35][N:36]3[CH:40]=[CH:39][N:38]=[N:37]3)[O:32][C:31]2=[O:41])[CH:14]=[CH:15][C:16]=1[C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH2:27][C@@H:26]([CH2:28][O:8][C:7]([C:2]3[CH:3]=[N:4][CH:5]=[CH:6][N:1]=3)=[O:9])[O:25][N:24]=2)=[N:19][CH:18]=1

Participants

7

Reactant 4

HCID 10472-Pyrazinecarboxylic acidHCID 6228DimethylformamideHCID 12734DiisopropylcarbodiimideHCID 9932836(5R)-3-(3-Fluoro-4-{6-[(5S)-5-(hydroxymethyl)-4,5-dihydroisoxazol-3-yl]pyridin-3-yl}phenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one

Product 1

HCID 58758434HCID 58758434, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Pyrazine-2-carboxylic acid (118 mg, 0.95 mMol), (5R)-3-(3-fluoro-4-{6-[(5S)-5-(hydroxymethyl)-4,5-dihydroisoxazol-3-yl]pyridin-3-yl}phenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (Example 1: 200 mg, 0.46 mMol), 4-(dimethylamino)pyridine (5 mg, 0.041 mmol) and DMF (2 ml) were combined and warmed to give a clear solution. The solution was allowed to cool to room temperature, and then diisopropylcarbodiimide (0.15 ml, 0.96 mmol) was added. The mixture was stirred for 18 hours, ethyl acetate was added, followed by washing with saturated NaCl. The organic layer was dried over sodium sulfate, evaporated, triturated with 1:5 ether:hexane, dissolved in 1:1 acetonitrile:methanol, adsorbed on silica gel and purified by chromatography (silica gel; elution with 1 to 10% methanol in dichloromethane). The product containing fractions were pooled and evaporated to give the title compound as a white solid, 159 mg.

Workup

  1. temperaturewarmed
  2. customto give a clear solution
  3. washby washing with saturated NaCl
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated
  6. customtriturated with 1:5 ether
  7. dissolutionhexane, dissolved in 1:1 acetonitrile
  8. custompurified by chromatography (silica gel; elution with 1 to 10% methanol in dichloromethane)
  9. additionThe product containing fractions
  10. customevaporated

Sources & evidence

ORD record
ord-fa9e2d6cb6464ef5b67a1ebe1fe085ac
Source dataset
uspto-grants-2007_03
Patent number
US07192974B2

Reaction notes

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