Dimethylformamide → HCID 66966216, compound

HRID 1711837Notes

Reaction equation

HRID 1711837 reaction equation
Br.Br[C:3]1C=C(CBr)C(N)=NC=1.[ClH:12].C[O:14][C:15](=[O:21])[C@@H:16]1[CH2:20][CH2:19][CH2:18][NH:17]1.[CH2:22]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[CH3:23].[CH3:29][N:30]([CH:32]=[O:33])C>O>[ClH:12].[O:33]=[C:32]1[C@H:27]2[N:24]([CH2:25][CH2:26][CH2:28]2)[CH2:22][C:23]2[CH:3]=[C:19](/[CH:20]=[CH:16]/[C:15]([OH:14])=[O:21])[CH:18]=[N:17][C:29]=2[NH:30]1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 8471TriethylamineHCID 2733200methyl L-prolinate hydrochlorideHCID 534200525-Bromo-3-(bromomethyl)pyridin-2-amine hydrobromide

Product 1

HCID 66966216HCID 66966216, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5-bromo-3-bromomethyl-pyridin-2-ylamine hydrobromide (6.00 g, 17.3 mmol) and L-proline methyl ester hydrochloride (2.88 g, 17.4 mmol) in DMF (125 mL) was treated with a solution of triethylamine (7.8 mL, 55.5 mmol) in DMF (75 mL). After stirring at room temperature under N2 for 3 h, the cloudy mixture was diluted with H2O (300 mL) and extracted with EtOAc (2×300 mL). The combined organic layers were washed with H2O (2×100 mL) and brine (100 mL), dried over Na2SO4, filtered and the solvent was removed in vacuo. Purification by flash column chromatography (silica gel, CH2Cl2/MeOH, 99:1 to 98:2) gave the title compound (3.66 g, 67%) as a pale yellow oil: MS (ESI) m/e 314 (M+H)+.

Workup

  1. extractionextracted with EtOAc (2×300 mL)
  2. washThe combined organic layers were washed with H2O (2×100 mL) and brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. customPurification by flash column chromatography (silica gel, CH2Cl2/MeOH, 99:1 to 98:2)

Sources & evidence

ORD record
ord-1c2f03594f4c42c78a8318db2265e5de
Source dataset
uspto-grants-2010_09
Patent number
US07790709B2

Reaction notes

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