Pyridine → HCID 59205098, compound

HRID 2425473Notes

Reaction equation

HRID 2425473 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-17da962583274c83bddf98ab99471a98
Source dataset
uspto-grants-2011_06
Patent number
US07964725B2

Reaction notes

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