Dimethylamine → HCID 90022178, compound

HRID 1754836Notes

Reaction equation

HRID 1754836 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14]2[N:17]=[C:18](Br)[S:19][C:13]=2[CH:12]1[C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[O:28][CH2:29][C:30]([OH:32])=[O:31])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:33][NH:34][CH3:35]>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14]2[N:17]=[C:18]([N:34]([CH3:35])[CH3:33])[S:19][C:13]=2[CH:12]1[C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[O:28][CH2:29][C:30]([OH:32])=[O:31])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 72949781HCID 72949781, compound

Product 1

HCID 90022178HCID 90022178, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (±)-2-bromo-4-(2-carboxymethoxy-5-chloro-phenyl)-6,7-dihydro-4H-thiazolo[5,4-c]pyridine-5-carboxylic acid benzyl ester (21 mg, 0.04 mmol, 1.0 eq.) in 2M dimethylamine in THF (0.5 mL) was heated at 80° C. for 18 hours. The reaction mixture was allowed to cool to r.t. and concentrated in vacuo. The residue was taken up in DMF, filtered, and purified by prep. HPLC (column: Atlantis, 30×75 mm, 10 um, UV/MS, acidic conditions) and concentrated in vacuo to give the title compound as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. filtrationfiltered
  3. custompurified by prep
  4. concentrationHPLC (column: Atlantis, 30×75 mm, 10 um, UV/MS, acidic conditions) and concentrated in vacuo

Sources & evidence

ORD record
ord-69cf0836f43347dbb8c3d004b52dd4ba
Source dataset
uspto-grants-2015_10
Patent number
US09169270B2

Reaction notes

Loading…