4-Chlorobenzylamine → HCID 10205007, compound

HRID 411223Notes

Reaction equation

HRID 411223 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.C[O-].[Na+].[CH3:13][N:14]1[C:19]2[CH:20]=[CH:21][C:22]([CH2:24][N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[CH:23][C:18]=2[S:17](=[O:32])(=[O:31])[C:16]([C:33](OC)=[O:34])=[N:15]1>CO>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:33]([C:16]2[S:17](=[O:31])(=[O:32])[C:18]3[CH:23]=[C:22]([CH2:24][N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)[CH:21]=[CH:20][C:19]=3[N:14]([CH3:13])[N:15]=2)=[O:34])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 660364-ChlorobenzylamineHCID 10942334Sodium MethoxideHCID 22397175HCID 22397175, compound

Product 1

HCID 10205007HCID 10205007, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
70 °C

Procedure

4-Chlorobenzylamine (0.66 mL) and a 0.5 M solution of NaOMe in CH3OH (0.060 mL) is added to a solution of methyl 1-methyl-6-(4-morpholinylmethyl)-1H-4,1,2-benzothiadiazine-3-carboxylate 4,4-dioxide (Preparation 41, 0.16 g) in CH3OH (15 mL) at room temperature. The mixture is heated for 12 hours at 70° C. and then the solvent is evaporated. The crude material is triturated with CH3CN and the organic layer is decanted. The remaining solid is chromatographed with MeOH/CH2Cl2 (1-5%) to obtain 0.174 g (83%) of the title compound as a white solid. Physical characteristics: MS (ESI+) m/z 463 (M+H).

Workup

  1. customthe solvent is evaporated
  2. customThe crude material is triturated with CH3CN
  3. customthe organic layer is decanted
  4. customThe remaining solid is chromatographed with MeOH/CH2Cl2 (1-5%)

Sources & evidence

ORD record
ord-c1b423b0d80a4199a2a5ede6c00eb30b
Source dataset
uspto-grants-2003_05
Patent number
US06559145B2

Reaction notes

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