(4S)-(4-methyl-2,5-dioxoimidazolidin-4-yl)methanesulphonyl chloride → HCID 11583056, compound

HRID 1441493Notes

Reaction equation

HRID 1441493 reaction equation
Cl.[CH:2]1([C:5]2[N:10]=[CH:9][C:8]([C:11]3[CH:12]=[C:13]4[C:18](=[CH:19][N:20]=3)[CH2:17][NH:16][CH2:15][CH2:14]4)=[CH:7][N:6]=2)[CH2:4][CH2:3]1.[CH3:21][C@@:22]1([CH2:29][S:30](Cl)(=[O:32])=[O:31])[C:26](=[O:27])[NH:25][C:24](=[O:28])[NH:23]1>C(Cl)Cl.C1COCC1>[CH:2]1([C:5]2[N:6]=[CH:7][C:8]([C:11]3[CH:12]=[C:13]4[C:18](=[CH:19][N:20]=3)[CH2:17][N:16]([S:30]([CH2:29][C@@:22]3([CH3:21])[NH:23][C:24](=[O:28])[NH:25][C:26]3=[O:27])(=[O:31])=[O:32])[CH2:15][CH2:14]4)=[CH:9][N:10]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 16738713(4S)-(4-methyl-2,5-dioxoimidazolidin-4-yl)methanesulphonyl chlorideHCID 66734806HCID 66734806, compound

Product 1

HCID 11583056HCID 11583056, compoundYield 67.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 6-(2-cyclopropylpyrimidin-5-yl)-1,2,3,4-tetrahydro-2,7-naphthyridine hydrochloride (0.12 g, 0.42 mmol) in DCM (10 mL) was added TEA (0.12 mL, 0.84 mmol) followed by the dropwise addition of [(4S)-4-methyl-2,5-dioxoimidazolidin-4-yl]methanesulfonyl chloride (0.090 g, 0.40 mmol) in THF (10 mL) at −10° C. The mixture was stirred at RT overnight, concentrated, taken up in water (10 mL) and extracted four times with EtOAc. The combined organic phases were dried, filtered and concentrated. Purification by prep-HPLC gave 0.12 g (64%) of the title compound as a white solid.

Workup

  1. concentrationconcentrated
  2. extractionextracted four times with EtOAc
  3. customThe combined organic phases were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification

Sources & evidence

ORD record
ord-3f074ce490804f8aaef5fc9fc0d46bd4
Source dataset
uspto-grants-2010_02
Patent number
US07655664B2

Reaction notes

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