Water → HCID 86628135, compound

HRID 2354101Notes

Reaction equation

HRID 2354101 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH2:13][C@@H:12]([NH:16][C:17]3[N:18]=[CH:19][C:20](/[CH:23]=[CH:24]/[C:25]([OH:27])=O)=[N:21][CH:22]=3)[CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH:29]1[O:34][NH2:35].C1C=CC2N(O)N=NC=2C=1.O>ClCCl>[C:1]1([CH2:7][CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH2:13][C@@H:12]([NH:16][C:17]3[N:18]=[CH:19][C:20](/[CH:23]=[CH:24]/[C:25]([NH:35][O:34][CH:29]4[CH2:30][CH2:31][CH2:32][CH2:33][O:28]4)=[O:27])=[N:21][CH:22]=3)[CH2:11]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 67129268HCID 67129268, compound

Product 1

HCID 86628135HCID 86628135, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of crude (2E)-3-[5-({(3R)-1-[3-phenylpropyl]- 3-piperidinyl}amino)-2-pyrazinyl] acrylic acid (345 mg), O-(tetrahydro-2H-pyran-2-yl)hydroxylamine (166 mg), and HOBT in dichloromethane (8.6 mL) was added WSCD (271 mg), which was stirred at room temperature for 17 hours. Water was added to the resultant. The organic layer was extracted and dried over Na2SO4, filtered, and evaporated in vacuo. The residue was purified by column chromatography on silica gel [chromatorexNH, 5 g, hexane:AcOEt=25:75) to give (2E)-3-[5-({(3R)-1-[3-phenylpropyl]-3-piperidinyl}amino)-2-pyrazinyl]-N-(tetrahydro-2H-pyran-2-yloxy)acrylamide (277 mg) as a pale yellow solid.

Workup

  1. additionwas added WSCD (271 mg), which
  2. extractionThe organic layer was extracted
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel [chromatorexNH, 5 g, hexane

Sources & evidence

ORD record
ord-d980032c326a49979c54d1dfc6c719f8
Source dataset
uspto-grants-2010_07
Patent number
US07750155B2

Reaction notes

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