Water → HCID 46846424, compound

HRID 2039664Notes

Reaction equation

HRID 2039664 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]3[C:10]([O:24][CH:25]([F:27])[F:26])=[CH:11][CH:12]=[C:13]([C:14]4[O:15][CH:16]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:18]=4)[C:7]=3[C:6]=2[CH:28]=1.N1C=CC=CC=1.[CH3:35][S:36](Cl)(=[O:38])=[O:37].O>O1CCCC1>[F:27][CH:25]([F:26])[O:24][C:10]1[C:8]2[O:9][C:5]3[CH:4]=[CH:3][C:2]([NH:1][S:36]([CH3:35])(=[O:38])=[O:37])=[CH:28][C:6]=3[C:7]=2[C:13]([C:14]2[O:15][CH:16]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:18]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 58496327HCID 58496327, compound

Product 1

HCID 46846424HCID 46846424, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(8-amino-4-(difluoromethoxy)dibenzo[b,d]furan-1-yl)oxazole-4-carboxylate (0.65 g, 1.667 mmol) in tetrahydrofuran (10 mL) was added pyridine (0.4 mL, 5.031 mmol). To this solution was added methane sulfonyl chloride (2.6 mL, 0.033 mol) at 0-5° C. After 30 minutes, the reaction slurry was stirred at room temperature for 18 hours. The reaction mass was poured into the cold water and extracted with dichloromethane (3×50 mL). The organics were dried over sodium sulphate and filtered. The organics were evaporated under reduced pressure to give the crude product. The product was purified by column chromatography by using gradient of ethyl acetate in hexane (0-20) %. Yield—44.8%. 1H-NMR (DMSO-d6) δ: 1.35-1.39 (m, 3H), 3.06 (s, 3H), 4.36-4.41 (m, 2H), 7.41 (s, 1H), 7.51 (d, 1H), 7.62 (d, 1H), 7.87 (d, 1H), 8.06 (d, 1H), 8.96 (s, 1H), 9.07 (s, 1H), 9.77 (s, 1H); HPLC (purity): 97.2%; Mass calculated for C20H16F2N2O7S-466.4, observed—467.0; Rf—0.47 (Ethyl acetate:Hexane (1:1)

Workup

  1. extractionextracted with dichloromethane (3×50 mL)
  2. dry with materialThe organics were dried over sodium sulphate
  3. filtrationfiltered
  4. customThe organics were evaporated under reduced pressure

Sources & evidence

ORD record
ord-5880acd6b12c42b18c4cb9eb6e30b2f5
Source dataset
uspto-grants-2013_11
Patent number
US08580795B2

Reaction notes

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