4-Methylmorpholine → tert-Butyl (2-{4-[({2-[(2,3-difluorobenzyl)thio]-6-methoxypyrimidin-4-yl}amino)sulfonyl]piperazin-1-yl}-2-oxoethyl)carbamate

HRID 1175523Notes

Reaction equation

HRID 1175523 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.ON1C2C=CC=CC=2N=N1.Cl.[F:25][C:26]1[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:33][S:34][C:35]1[N:40]=[C:39]([NH:41][S:42]([N:45]2[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]2)(=[O:44])=[O:43])[CH:38]=[C:37]([O:51][CH3:52])[N:36]=1.CN1CCOCC1>CN(C=O)C>[F:25][C:26]1[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:33][S:34][C:35]1[N:40]=[C:39]([NH:41][S:42]([N:45]2[CH2:46][CH2:47][N:48]([C:10](=[O:12])[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:49][CH2:50]2)(=[O:43])=[O:44])[CH:38]=[C:37]([O:51][CH3:52])[N:36]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 27960291-Hydroxybenzotriazole hydrateHCID 131728548N-[2-[[(2,3-Difluorophenyl)methyl]thio]-6-methoxypyrimidin-4-yl]piperazine-1-sulfonamide, hydrochloride salt2×

Product 1

HCID 86619892tert-Butyl (2-{4-[({2-[(2,3-difluorobenzyl)thio]-6-methoxypyrimidin-4-yl}amino)sulfonyl]piperazin-1-yl}-2-oxoethyl)carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of N-(tert-butoxycarbonyl)glycine (0.11 g) in DMF (10 mL) was added 1,3-Dicyclohexycarbodiimide (0.14 g) and 1-hydroxybenzotriazole hydrate (94 mg). After stirring at room temperature for 1 h, a solution of N-[2-[[(2,3-Difluorophenyl)methyl]thio]-6-methoxypyrimidin-4-yl]piperazine-1-sulfonamide, hydrochloride salt (the product of step i, 0.27 g) and N-methylmorpholine (78 μL) in DMF (5 mL) was added dropwise and stirring continued at room temperature for 24 h. The mixture was filtered, rinsed with DCM and the filtrate evaporated. The crude material was purified by column chromatography on silica gel using EtOAc/isohexane (3:2) as eluent to give the subtitle compound as a foam. Yield: 0.24 g

Workup

  1. stirringstirring
  2. waitcontinued at room temperature for 24 h
  3. filtrationThe mixture was filtered
  4. washrinsed with DCM
  5. customthe filtrate evaporated
  6. customThe crude material was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-e15ca2f0720e423db8f66ebfb931cbd6
Source dataset
uspto-grants-2010_11
Patent number
US07838675B2

Reaction notes

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