Dimethylamine → N-(7-dimethylaminomethyl-1-methyl-2,2-dioxo-1,2,3,4-tetrahydro-2lambda6-benzo[c][1,2]thiazin-4-yl)-3-(naphthalen-2-yl-sulfonylamino)-3-phenyl-propionamide

HRID 32087Notes

Reaction equation

HRID 32087 reaction equation
CS(OS(C)(=O)=O)(=O)=O.O[CH2:11][C:12]1[CH:13]=[CH:14][C:15]2[CH:20]([NH:21][C:22](=[O:45])[CH2:23][CH:24]([NH:31][S:32]([C:35]3[CH:44]=[CH:43][C:42]4[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=4)[CH:36]=3)(=[O:34])=[O:33])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:19][S:18](=[O:47])(=[O:46])[N:17]([CH3:48])[C:16]=2[CH:49]=1.[CH3:50][N:51]1CCOC[CH2:52]1.N(C)C.S([O-])(=O)(=O)C>C(Cl)Cl.C1COCC1>[CH3:50][N:51]([CH2:11][C:12]1[CH:13]=[CH:14][C:15]2[CH:20]([NH:21][C:22](=[O:45])[CH2:23][CH:24]([NH:31][S:32]([C:35]3[CH:44]=[CH:43][C:42]4[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=4)[CH:36]=3)(=[O:33])=[O:34])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:19][S:18](=[O:47])(=[O:46])[N:17]([CH3:48])[C:16]=2[CH:49]=1)[CH3:52]

Participants

8

Reactant 5

HCID 674DimethylamineHCID 79724-MethylmorpholineHCID 81560Methanesulfonic anhydrideHCID 85257MethanesulfonateHCID 68926983HCID 68926983, compound

Product 1

HCID 68929010N-(7-dimethylaminomethyl-1-methyl-2,2-dioxo-1,2,3,4-tetrahydro-2lambda6-benzo[c][1,2]thiazin-4-yl)-3-(naphthalen-2-yl-sulfonylamino)-3-phenyl-propionamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methanesulfonic anhydride (100 mg, 0.55 mmol) was added to a THF (5 mL) solution of N-(7-hydroxymethyl-1-methyl-2,2-dioxo-1,2,3,4-tetrahydro-2λ6-benzo[c][1,2]thiazin-4-yl)-3-(naphthalen-2-yl-sulfonylamino)-3-phenyl-propionamide (Step D) (200 mg, 0.345 mmol) and N-methylmorpholine (0.11 mL, 0.55 mmol). After 30 min stirring, Me2NH (1.73 mL, 3.45 mmol, 2.0 M in THF) was added to this freshly prepared mesylate solution. After stirring overnight, the mixture was diluted with CH2Cl2 (30 mL), washed with H2O, dried over MgSO4, filtered, and concentrated in vacuo. Chromatography on silica (0-5% MeOH in CH2Cl2) provided the title compound. MS (+ESI, m/z): 607 (M+H)+.

Workup

  1. stirringAfter stirring overnight
  2. washwashed with H2O
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-323053c384dd4aecb9ececb9ae2896d2
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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