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

HRID 38075

Reaction equation

HRID 38075 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:8]([C:15]3[CH:16]=[C:17]([NH2:21])[CH:18]=[CH:19][CH:20]=3)=[N:9][N:10]3[CH2:14][CH2:13][S:12][C:11]=23)=[CH:3][CH:2]=1.[F:22][C:23]1[CH:24]=[C:25]([S:29](Cl)(=[O:31])=[O:30])[CH:26]=[CH:27][CH:28]=1.CN1CCOCC1>C(Cl)Cl>[F:22][C:23]1[CH:24]=[C:25]([S:29]([NH:21][C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([C:8]3[C:7]([C:4]4[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=4)=[C:11]4[S:12][CH2:13][CH2:14][N:10]4[N:9]=3)[CH:16]=2)(=[O:31])=[O:30])[CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 27342583-Fluorobenzenesulfonyl ChlorideHCID 469291833-(7-Pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-phenylamine

Product 1

HCID 584770903-fluoro-N-[3-(7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-phenyl]-benzenesulfonamideYield 58.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-(7-Pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-phenylamine (prepared as described in Example 1) (30 mg, 0.102 mmol) was dissolved in dry DCM (1 mL). At room temperature 3-fluorobenzensulfonylchloride (0.014 mL, 0.107 mmol, 1.05 eq) was added followed by NMM (0.012 mL, 0.107 mmol, 1.05 eq) and the mixture was stirred for 1 hour. 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 96:4) to give 27 mg of 3-fluoro-N-[3-(7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-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 96:4)

Sources & evidence

ORD record
ord-66e88c0f0e00469c854c41e01f9ef212
Source dataset
uspto-grants-2013_09
Patent number
US08524707B2

Linked notes

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