Pyridine → HCID 178500684, compound

HRID 1713796Notes

Reaction equation

HRID 1713796 reaction equation
Cl[C:2](=[O:7])[C:3]([O:5][CH3:6])=[O:4].[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]2[CH2:20][CH2:19][C@H:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH2:17][CH2:16]2)=[CH:11][CH:10]=1.N1C=CC=CC=1>C(Cl)Cl>[CH3:25][O:24][C:22](=[O:23])[CH2:21][C@H:18]1[CH2:17][CH2:16][C@H:15]([C:12]2[CH:11]=[CH:10][C:9]([NH:8][C:2](=[O:7])[C:3]([O:5][CH3:6])=[O:4])=[CH:14][CH:13]=2)[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 79846Methyl chloroglyoxylateHCID 178500653HCID 178500653, compound

Product 1

HCID 178500684HCID 178500684, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl chloro(oxo)acetate (0.842 mL) was added to a stirred solution of methyl [trans-4-(4-aminophenyl)cyclohexyl]acetate (1740 mg) and pyridine (0.689 mL) in DCM (50 mL) at 0° C. After the addition was complete the mixture was allowed to warm to ambient temperature and stirred for 64 hours. The solution was diluted with DCM (100 mL), washed with water (50 mL) and brine (50 mL), then dried and concentrated in vacuo to give the title compound (2267 mg) as a solid; 1H NMR δ 7.60 (2H, d), 7.18 (2H, d), 3.83 (3H, s), 3.58 (3H, s), 2.58-35 (1H+DMSO, m), 2.21 (2H, d), 1.75 (5H, m), 1.43 (2H, m), 1.12 (2H, m); MS m/e MH− 332.

Workup

  1. additionAfter the addition
  2. washwashed with water (50 mL) and brine (50 mL)
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1889c2b9165441779f181ab59cfd58a7
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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