Hydrochloric Acid → HCID 18317247, compound

HRID 1700127Notes

Reaction equation

HRID 1700127 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7](=[O:19])[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)=[CH:3][CH:2]=1.[H-].[Na+].Cl[CH2:23][C:24]([CH:26]1[CH2:31][CH2:30][N:29]([C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])[CH2:28][CH2:27]1)=[O:25].Cl.C([O-])([O-])=O.[Na+].[Na+]>CS(C)=O>[N:1]1[CH:2]=[CH:3][C:4]([C:7](=[O:19])[CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:17])([F:18])[F:16])[CH:10]=2)[CH2:23][C:24](=[O:25])[CH:26]2[CH2:31][CH2:30][N:29]([C:32]([O:34][CH2:35][C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)=[O:33])[CH2:28][CH2:27]2)=[CH:5][CH:6]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 24758Sodium hydrideHCID 18317254HCID 18317254, compoundHCID 23000504HCID 23000504, compound

Product 1

HCID 18317247HCID 18317247, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Under Ar, a solution of 33 (5.2 g, 19.6 mmol) in DMSO (65 mL) was stirred at room temperature and treated with 95% NaH (0.58 g, 22.8 mmol). After 1 h, a solution of 5 (5.8 g, 19.6 mmol) in DMSO (25 mL) was added dropwise. After 18 h, the reaction was poured into 2N HCl (100 mL) and then basified with saturated Na2CO3 and then extracted with EtOAc (3×). The combined EtOAc extracts were backwashed with H2O, brine, dried, filtered and concentrated to dryness. The residue was chromatographed on a Still column to yield 3.3 g of crude 34.

Workup

  1. waitAfter 18 h
  2. extractionextracted with EtOAc (3×)
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe residue was chromatographed on a Still column
  7. customto yield 3.3 g of crude 34

Sources & evidence

ORD record
ord-bcf15d532a5c4c69bd0565bf29294b26
Source dataset
uspto-grants-2002_02
Patent number
US06350744B1

Reaction notes

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