O-(Tetrahydropyran-2-yl)hydroxylamine → HCID 86628128, compound

HRID 2354087Notes

Reaction equation

HRID 2354087 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][N:10]2[CH2:14][CH2:13][C@@H:12]([NH:15][C:16]3[N:17]=[CH:18][C:19](/[CH:22]=[CH:23]/[C:24]([OH:26])=O)=[N:20][CH:21]=3)[CH2:11]2)[CH:5]=[CH:6][CH:7]=1.[NH2:27][O:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][O:30]1>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][N:10]2[CH2:14][CH2:13][C@@H:12]([NH:15][C:16]3[N:17]=[CH:18][C:19](/[CH:22]=[CH:23]/[C:24]([NH:27][O:28][CH:29]4[CH2:34][CH2:33][CH2:32][CH2:31][O:30]4)=[O:26])=[N:20][CH:21]=3)[CH2:11]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 67128803HCID 67128803, compound

Product 1

HCID 86628128HCID 86628128, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (2E)-3-[5-({(3R)-1-[2-(3-fluorophenyl)ethyl]-3-pyrrolidinyl}amino)-2-pyrazinyl]acrylic acid (226 mg) and 2-(aminooxy)tetrahydro-2H-pyran and WSCD-HCl was stirred for 24 hours at ambient temperature. CH2Cl2 was added the mixture. The CH2Cl2 layer was washed with water and evaporated in vacuo. The residue was chromatographed on silica gel using a mixture of CHCl3-MeOH (10:1) to give (2E)-3-[5-({(3R)-1-[2-(3-fluorophenyl)ethyl]-3-pyrrolidinyl}amino)-2-pyrazinyl]-N-(tetrahydro-2H-pyran-2-yloxy)acrylamide (160 mg) as a solid.

Workup

  1. washThe CH2Cl2 layer was washed with water
  2. customevaporated in vacuo
  3. customThe residue was chromatographed on silica gel using
  4. additiona mixture of CHCl3-MeOH (10:1)

Sources & evidence

ORD record
ord-08bdb30a89c04229a79553292f30683f
Source dataset
uspto-grants-2010_07
Patent number
US07750155B2

Reaction notes

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