Dimethylformamide → HCID 86713254, compound

HRID 927867Notes

Reaction equation

HRID 927867 reaction equation
CN(C)CC[CH2:5][C:6]([C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[S:15]([NH:18][C:19]1[C:28]([C:29]([O:31]C)=[O:30])=[C:27]2[C:22]([CH:23]3[CH2:33][CH:24]3[CH2:25][O:26]2)=[CH:21][CH:20]=1)(=[O:17])=[O:16])=[O:7].C(=O)([O-])[O-].[K+].[K+].N1C=C[C:43](N)=N1.[I-].[Li+].[CH3:49][N:50]([CH:52]=O)[CH3:51]>CO.C(O)=O>[CH3:51][N:50]([CH3:49])[CH:52]([CH3:43])[CH2:5][C:6]([C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[S:15]([NH:18][C:19]1[C:28]([C:29]([OH:31])=[O:30])=[C:27]2[C:22]([CH:23]3[CH2:33][CH:24]3[CH2:25][O:26]2)=[CH:21][CH:20]=1)(=[O:17])=[O:16])=[O:7]

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 66321Lithium iodideHCID 86713255HCID 86713255, compound2×HCID 178418806HCID 178418806, compound

Product 1

HCID 86713254HCID 86713254, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of methyl (1aRS,7bSR)-5-[2-(4-dimethylaminobutyryl)-4-fluorobenzenesulfonyl-amino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (Intermediate 108, 0.2 g), potassium carbonate (0.22 g), 1H-pyrazole-3-amine (0.34 g) and lithium iodide (1.07 g) in DMF (10 mL) was irradiated in the microwave at 150° C. for 1 hour. After cooling, the mixture was diluted with methanol and acidified to pH 3 with formic acid then concentrated under vacuum. The residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM (5%). The resultant product was purified by HPLC (C18) to give (1aRS,7bSR)-5-[2-(3-dimethylaminobutyryl)-4-fluorobenzenesulfonyl-amino]-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylic acid (0.03 g) as a white solid.

Workup

  1. customwas irradiated in the microwave at 150° C. for 1 hour
  2. temperatureAfter cooling
  3. concentrationthen concentrated under vacuum
  4. customThe residue was purified by chromatography on silica
  5. washeluting with a mixture of methanol and DCM (5%)
  6. customThe resultant product was purified by HPLC (C18)

Sources & evidence

ORD record
ord-075e9ec8873f42c6a43a967bc7d3bd36
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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