Water → tert-Butyl (5-{6-[(tert-butoxycarbonyl)(methyl)amino]-1,3-benzothiazol-2-yl}pyridin-2-yl)methylcarbamate

HRID 1698109Notes

Reaction equation

HRID 1698109 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][C:11]1[CH:34]=[CH:33][C:14]2[N:15]=[C:16]([C:18]3[CH:19]=[CH:20][C:21]([CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[N:22][CH:23]=3)[S:17][C:13]=2[CH:12]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:35]I.O>CN(C=O)C>[C:3]([O:7][C:8]([N:10]([CH3:35])[C:11]1[CH:34]=[CH:33][C:14]2[N:15]=[C:16]([C:18]3[CH:19]=[CH:20][C:21]([CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[N:22][CH:23]=3)[S:17][C:13]=2[CH:12]=1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86626544Tert-butyl (5-{6-[(tert-butoxycarbonyl)amino]-1,3-benzothiazol-2-yl}pyridin-2-yl)methylcarbamate

Product 1

HCID 86626545tert-Butyl (5-{6-[(tert-butoxycarbonyl)(methyl)amino]-1,3-benzothiazol-2-yl}pyridin-2-yl)methylcarbamateYield 91.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

NaH (95%, 4.5 mg, 0.18 mmol) was added to a solution of tert-butyl (5-{6-[(tert-butoxycarbonyl)amino]-1,3-benzothiazol-2-yl}pyridin-2-yl)methylcarbamate (66 mg, 0.14 mmol) in DMF (2 mL). The mixture was cooled to 0° C. and MeI (10 μL, 0.16 mmol) was added. The reaction was stirred at rt on. Water was added and the mixture was extracted with EtOAc (3×) The combined organic phases were dried (MgSO4) and concentrated. Flash chromatography (Heptane/EtOAc gradient) gave the product (60 mg) as a white solid. MS m/z (M+H) 471.

Workup

  1. extractionthe mixture was extracted with EtOAc (3×) The combined organic phases
  2. dry with materialwere dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d14d48f026bb4f819b35c298c724f3b6
Source dataset
uspto-grants-2012_04
Patent number
US08163928B2

Reaction notes

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