Triethylamine → HCID 178500685, compound

HRID 1713825Notes

Reaction equation

HRID 1713825 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[CH2:14][CH2:13][C@H:12]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH2:11][CH2:10]2)=[N:7][CH:8]=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@H:12]1[CH2:11][CH2:10][C@H:9]([C:6]2[N:7]=[CH:8][C:3]([NH:2][C:28](=[O:33])[C:29]([O:31][CH3:32])=[O:30])=[CH:4][CH:5]=2)[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79846Methyl chloroglyoxylateHCID 178500657HCID 178500657, compound

Product 1

HCID 178500685HCID 178500685, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice water cooled solution of methyl [trans-4-(5-aminopyridin-2-yl)cyclohexyl]acetate hydrochloride, prepared as above, (831 mg, 2.59 mmol) in DCM (50 mL) was added triethylamine (1.3 mL, 9.31 mmol) followed by methyl chlorooxoacetate (0.31 mL, 3.36 mmol) and the reaction mixture was allowed to stir at O—C for 2 hrs. The reaction mixture was diluted with DCM (100 mL) and washed with water (80 mL) then brine (80 mL) and the aqueous layer was re extracted with DCM (50 mL). The organic washings were combined, dried and concentrated to give the title compound, 865 mg (2.59 mmol, 100%) which was taken through to the next stage; 1H NMR (CDCl3) δ 1.13-1.27 (m, 1H), 1.57-1.64 (m, 3H), 1.84-2.00 (m, 5H), 2.26 (d, 2H), 2.62-2.70 (m, 1H), 3.68 (s, 3H), 3.98 (s, 3H), 7.18 (d, 1H), 8.13 (d, 1H), 8.60 (s, 1H), 8.82 (brs, 1H); MS m/e MH+ 335.

Workup

  1. washwashed with water (80 mL)
  2. extractionbrine (80 mL) and the aqueous layer was re extracted with DCM (50 mL)
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f44b9ebbafe4417cbc37083176a96ca6
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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