4-Methylmorpholine → 3-fluoro-N-[3-(3-pyridin-4-yl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]thiazin-2-yl)-phenyl]-benzenesulfonamide

HRID 38078Notes

Reaction equation

HRID 38078 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:8]([C:16]3[CH:17]=[C:18]([NH2:22])[CH:19]=[CH:20][CH:21]=3)=[N:9][N:10]3[CH2:15][CH2:14][CH2:13][S:12][C:11]=23)=[CH:3][CH:2]=1.[F:23][C:24]1[CH:25]=[C:26]([S:30](Cl)(=[O:32])=[O:31])[CH:27]=[CH:28][CH:29]=1.CN1CCOCC1>C(Cl)Cl>[F:23][C:24]1[CH:25]=[C:26]([S:30]([NH:22][C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([C:8]3[C:7]([C:4]4[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=4)=[C:11]4[S:12][CH2:13][CH2:14][CH2:15][N:10]4[N:9]=3)[CH:17]=2)(=[O:32])=[O:31])[CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 27342583-Fluorobenzenesulfonyl ChlorideHCID 674228643-(3-Pyridin-4-yl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]thiazin-2-yl)-phenylamine

Product 1

HCID 467018383-fluoro-N-[3-(3-pyridin-4-yl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]thiazin-2-yl)-phenyl]-benzenesulfonamideYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-(3-Pyridin-4-yl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]thiazin-2-yl)-phenylamine (prepared as described in Example 3) (30 mg, 0.097 mmol) was dissolved in dry DCM (1 mL). At room temperature 3-fluorobenzensulfonylchloride (0.013 mL, 0.097 mmol, 1 eq) was added followed by NMM (0.011 mL, 0.097 mmol, 1 eq) and the mixture was stirred for 2 hours. It was then diluted with DCM and washed with water and brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (eluant DCM/MeOH/NH3 7 N in MeOH 95:5:0.5) to give 42 mg (93%) of 3-fluoro-N-[3-(3-pyridin-4-yl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]thiazin-2-yl)-phenyl]-benzenesulfonamide.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by chromatography on silica gel (eluant DCM/MeOH/NH3 7 N in MeOH 95:5:0.5)

Sources & evidence

ORD record
ord-baf1201d628e4cbf87e1d07953b45795
Source dataset
uspto-grants-2013_09
Patent number
US08524707B2

Reaction notes

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