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

HRID 1025015Notes

Reaction equation

HRID 1025015 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].C1(N=C=NC2CCCCC2)CCCCC1.O.ON1C2C=CC=CC=2N=N1.Cl.[F:40][C:41]1[C:46]([F:47])=[CH:45][CH:44]=[CH:43][C:42]=1[CH2:48][S:49][C:50]1[N:55]=[C:54]([NH:56][S:57]([N:60]2[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]2)(=[O:59])=[O:58])[CH:53]=[C:52]([O:66][CH3:67])[N:51]=1.CN1CCOCC1>CN(C=O)C>[F:40][C:41]1[C:46]([F:47])=[CH:45][CH:44]=[CH:43][C:42]=1[CH2:48][S:49][C:50]1[N:55]=[C:54]([NH:56][S:57]([N:60]2[CH2:61][CH2:62][N:63]([C:10](=[O:12])[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:64][CH2:65]2)(=[O:58])=[O:59])[CH:53]=[C:52]([O:66][CH3:67])[N:51]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 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-Dicyclohexylcarbodiimide (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-36113c74a68643328ef33e460d1eb648
Source dataset
uspto-grants-2014_05
Patent number
US08722883B2

Reaction notes

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