Hydrochloric Acid → N-[2-[[(1R)-2,3-dihydro-1H-inden-1-yl]amino]-4H-3,1-benzoxazin-5-yl]-3,5-difluorobenzenesulfonamide

HRID 1666107Notes

Reaction equation

HRID 1666107 reaction equation
[C@H:1]1([NH:10][C:11]2[O:12][CH2:13][C:14]3[C:20]([NH2:21])=[CH:19][CH:18]=[CH:17][C:15]=3[N:16]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[F:22][C:23]1[CH:24]=[C:25]([S:30](Cl)(=[O:32])=[O:31])[CH:26]=[C:27]([F:29])[CH:28]=1.Cl>N1C=CC=CC=1>[F:29][C:27]1[CH:26]=[C:25]([S:30]([NH:21][C:20]2[C:14]3[CH2:13][O:12][C:11]([NH:10][C@H:1]4[C:9]5[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=5)[CH2:3][CH2:2]4)=[N:16][C:15]=3[CH:17]=[CH:18][CH:19]=2)(=[O:31])=[O:32])[CH:24]=[C:23]([F:22])[CH:28]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 27740583,5-Difluorobenzenesulfonyl chlorideHCID 178507384HCID 178507384, compound

Product 1

HCID 178527468N-[2-[[(1R)-2,3-dihydro-1H-inden-1-yl]amino]-4H-3,1-benzoxazin-5-yl]-3,5-difluorobenzenesulfonamideYield 9.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(R)—N2-Indan-1-yl-4H-benzo[d][1,3]oxazine-2,5-diamine (example 2) (150 mg, 0.54 mmol) was dissolved in 5 mL pyridine and 3,5-difluoro-benzenesulfonyl chloride (112 mg, 0.53 mmol) was added. The reaction mixture was stirred at room temperature overnight. 1N HCl was added until pH5. The mixture was extracted three times with ethyl acetate (50 mL each). The organic phases ware pooled, dried with sodium sulfate, filtered and evaporated. The crude product was purified by a silica gel column chromatography with heptane/ethyl acetate 1:1 to give a white solid (24 mg, 9%), MS: m/e=456.0 (M+H+).

Workup

  1. extractionThe mixture was extracted three times with ethyl acetate (50 mL each)
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified by a silica gel column chromatography with heptane/ethyl acetate 1:1

Sources & evidence

ORD record
ord-4330ee1d40774dee9a2b5beb5255da06
Source dataset
uspto-grants-2011_10
Patent number
US08044047B2

Reaction notes

Loading…