3-Amino-2-methoxypyridine → HCID 66935586, compound

HRID 1028209Notes

Reaction equation

HRID 1028209 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH:18][C:19](OC3C=CC([N+]([O-])=O)=CC=3)=[O:20])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:31][C:32]1[C:33]([O:38][CH3:39])=[N:34][CH:35]=[CH:36][CH:37]=1>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH:18][C:19]([NH:31][C:32]3[C:33]([O:38][CH3:39])=[N:34][CH:35]=[CH:36][CH:37]=3)=[O:20])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 27374883-Amino-2-methoxypyridineHCID 66935714HCID 66935714, compound

Product 1

HCID 66935586HCID 66935586, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-(4-nitro-phenoxycarbonylamino)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (1.46 g) obtained in Example (24a), 3-amino-2-methoxypyridine (441 mg), and acetonitrile (20 mL) was heated to reflux for 5 hours and concentrated. The residue was diluted with ethyl acetate, then washed with a saturated aqueous solution of sodium bicarbonate (twice) and brine, and then concentrated. The residue was purified by chromatography (dichloromethane/ethyl acetate) to obtain the title compound (770 mg, 55%) as an off-white foam.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 hours
  3. concentrationconcentrated
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed with a saturated aqueous solution of sodium bicarbonate (twice) and brine
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-8252aa7aa3974c8ab611f206dc7100d0
Source dataset
uspto-grants-2014_05
Patent number
US08735425B2

Reaction notes

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