Dichloromethane → HCID 68836920, compound

HRID 1787925Notes

Reaction equation

HRID 1787925 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]([O:10][CH3:11])=[O:9].C([C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[C:18]([O:25][CH:26]2[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]2)[CH:17]=1)(C)(C)C.C(N(CC)[CH:43]([CH3:45])[CH3:44])(C)C.Cl[CH2:49]Cl>C(OCC)(=O)C>[C:43]([C:2]1([NH:1][C:20](=[O:21])[C:19]2[CH:23]=[CH:24][CH:16]=[CH:17][C:18]=2[O:25][CH:26]2[CH2:27][CH2:28][N:29]([C:32]([O:34][C:35]([CH3:36])([CH3:37])[CH3:38])=[O:33])[CH2:30][CH2:31]2)[CH:7]=[CH:6][N:5]=[CH:4][CH:3]1[C:8]([O:10][CH3:11])=[O:9])([CH3:45])([CH3:49])[CH3:44]

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 81531DiisopropylethylamineHCID 592353Methyl 4-aminopyridine-3-carboxylateHCID 86610260HCID 86610260, compound

Product 1

HCID 68836920HCID 68836920, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirring suspension of methyl 4-aminopyridine-3-carboxylate (0.10 g, 0.659 mmol) in dichloromethane (1 mL) was added a solution of 4-tert-butyl-2-(1-Boc-piperidin-4-yloxy)benzoyl chloride (1.3 mmol) in dichloromethane (6 mL), followed by N,N-diisopropylethylamine (0.15 mL, 0.8 mmol) and 4-N,N-dimethylaminopyridine (0.0084 g, 0.068 mmol). After stirring overnight, the solution was diluted with ethyl acetate and washed three times with satd aq NaHCO3. The combined aq phase was back extracted with ethyl acetate and the combined organic phase was dried with MgSO4, filtered and concentrated in vacuo. The residue was chromatographed over silica gel, eluting with a gradient of 30% ethyl acetate in hexanes through 100% ethyl acetate. The product containing fractions were combined and concentrated in vacuo to give the title compound (0.223 g, 66%) as a thick yellow syrup.

Workup

  1. washwashed three times with satd aq NaHCO3
  2. extractionThe combined aq phase was back extracted with ethyl acetate
  3. dry with materialthe combined organic phase was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed over silica gel
  7. washeluting with a gradient of 30% ethyl acetate in hexanes through 100% ethyl acetate
  8. additionThe product containing fractions
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a4e122a776584622b446483b34fbc154
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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