Pyridine → HCID 59205098, compound

HRID 2241927Notes

Reaction equation

HRID 2241927 reaction equation
ClC(N(C)C)=C(C)C.[F:9][CH:10]([F:33])[O:11][CH2:12][C@@H:13]([O:15][C:16]1[CH:17]=[C:18]([CH:22]=[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=1)[C:19]([OH:21])=O)[CH3:14].[CH3:34][C:35]1[N:36]=[CH:37][C:38]([NH2:41])=[N:39][CH:40]=1.N1C=CC=CC=1>C(Cl)Cl>[F:33][CH:10]([F:9])[O:11][CH2:12][C@@H:13]([O:15][C:16]1[CH:17]=[C:18]([CH:22]=[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=1)[C:19]([NH:41][C:38]1[CH:37]=[N:36][C:35]([CH3:34])=[CH:40][N:39]=1)=[O:21])[CH3:14]

Participants

6

Reactant 4

HCID 1049PyridineHCID 3132155-Methylpyrazin-2-amineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 591271733-[(2S)-1-(difluoromethoxy)propan-2-yl]oxy-5-phenylmethoxy-benzoic acid

Product 1

HCID 59205098HCID 59205098, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Chloro-N,N,2-trimethyl-prop-1-en-1-amine (0.26 mL, 2.0 mmol) was added to a solution of 3-[(2S)-1-(difluoromethoxy)propan-2-yl]oxy-5-phenylmethoxy-benzoic acid (0.54 g, 1.5 mmol) in DCM (20 mL) and stirred for 1 hour. 5-Methylpyrazin-2-amine (CAS no. 5521-58-4) (335 mg, 3.1 mmol) then pyridine (0.25 mL, 3.1 mmol) were added and the reaction stirred for a further 30 minutes before being reduced in vacuo and partitioned between ethyl acetate (50 mL) and water (50 mL). The aqueous layer was further extracted into ethyl acetate (50 mL) and the combined organics washed with water (50 mL), brine (50 mL), dried (MgSO4), and reduced in vacuo. The crude residue was chromatographed on silica, eluting with 40-100% ethyl acetate in isohexane, to give the desired compound (0.48 g).

Workup

  1. stirringthe reaction stirred for a further 30 minutes
  2. custompartitioned between ethyl acetate (50 mL) and water (50 mL)
  3. extractionThe aqueous layer was further extracted into ethyl acetate (50 mL)
  4. washthe combined organics washed with water (50 mL), brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. customThe crude residue was chromatographed on silica
  7. washeluting with 40-100% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-b3f9f14437ed4b63b2bffa1faf235d6a
Source dataset
uspto-grants-2010_03
Patent number
US07671060B2

Reaction notes

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