HCID 57771778, compound → HCID 57771701, compound

HRID 1174944Notes

Reaction equation

HRID 1174944 reaction equation
[CH3:1][N:2]([CH2:6][CH2:7][N:8]([CH3:21])[C:9]1[S:10][C:11]2[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[CH:14][C:12]=2[N:13]=1)[C:3](=[O:5])[CH3:4]>C(O)C.C1COCC1.[Pd]>[NH2:18][C:16]1[CH:15]=[CH:14][C:12]2[N:13]=[C:9]([N:8]([CH3:21])[CH2:7][CH2:6][N:2]([CH3:1])[C:3](=[O:5])[CH3:4])[S:10][C:11]=2[CH:17]=1

Participants

5

Reactant 1

HCID 57771778HCID 57771778, compound

Product 1

HCID 57771701HCID 57771701, compoundYield 77.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Shake a mixture of N-methyl-N-{2-[methyl-(6-nitro-benzothiazol-2-yl)-amino]-ethyl}-acetamide (0.30 g, mmol) and Pd/C (5%, 0.1515 g) in absolute ethanol (50 mL) and anhydrous THF (20 mL) under 60 psi H2(g) at room temperature for 18 h. Filter the mixture and concentrate in vacuo. Residue re-subjected to hydrogenation using Pd/C (0.2101 g) in absolute ethanol (50 mL) and THF (10 mL) to yield the desired product (0.209 g). Adsorb onto silica gel and subject to silica gel flash column chromatography (12 g column, eluting with 1-5% MeOH/CH2Cl2). Adsorbed on a Silicycle cartridge (Si-Tosic Acid, 35 mL, 10 g) washing with MeOH and eluted with 2N NH3 in MeOH. The product is 70% pure by LC-MS (0.146 g, %). mass spectrum (m/e): 279.0 (M+1). Used without further purification.

Workup

  1. filtrationFilter the mixture
  2. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-b1c2f001406b49cda8f279827cc643c1
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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