Triethylamine → HCID 59464186, compound

HRID 1713919Notes

Reaction equation

HRID 1713919 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][C:11]([CH2:15][C:16]([O:18][CH3:19])=[O:17])([CH3:14])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.C(N(CC)CC)C.Cl[C:28](=[O:33])[C:29]([O:31][CH3:32])=[O:30]>C(Cl)Cl>[CH3:19][O:18][C:16](=[O:17])[CH2:15][C:11]1([CH3:14])[CH2:12][CH2:13][N:8]([C:5]2[N:6]=[CH:7][C:2]([NH:1][C:28](=[O:33])[C:29]([O:31][CH3:32])=[O:30])=[CH:3][CH:4]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79846Methyl chloroglyoxylateHCID 59464333HCID 59464333, compound

Product 1

HCID 59464186HCID 59464186, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl [1-(5-aminopyridin-2-yl)-4-methylpiperidin-4-yl]acetate (3.29 g, 13.20 mmol) in DCM (100 mL) was added triethylamine (2.2 mL, 15.84 mmol) followed by methyl chlorooxoacetate (1.6 mL, 17.15 mmol) and the reaction mixture was allowed to stir at ambient temperature for 1.5 hrs. The reaction mixture was washed brine (2×100 mL), the aqueous layer was re extracted with DCM (50 mL) the organic washings were combined, dried and concentrated to leave the title compound as a brown gum (4.4 g, 13.2 mmol, 100%). 1H NMR δ 1.06 (s, 3H), 1.40-1.46 (m, 2H), 1.53-1.57 (m, 2H), 2.36 (s, 3H), 3.46-3.52 (m, 2H), 3.59 (s, 3H), 3.67-3.73 (m, 2H), 3.78 (s, 3H), 6.90 (d, 1H), 7.56 (d, 1H), 8.06 (s, 1H); MS m/e MH+ 350.

Workup

  1. washThe reaction mixture was washed brine (2×100 mL)
  2. extractionthe aqueous layer was re extracted with DCM (50 mL) the organic washings
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5003621c71984f8c885b8b88483bdb32
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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