Triethylamine → HCID 178491484, compound

HRID 1247250Notes

Reaction equation

HRID 1247250 reaction equation
[C:1]([C:3]1[CH:24]=[CH:23][C:6]([CH2:7][NH:8][C:9](=[O:22])[CH:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=2[F:21])[O:11][CH3:12])=[CH:5][CH:4]=1)#[N:2].Cl.[NH2:26][OH:27].C(N(CC)CC)C>CO>[F:21][C:14]1[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:13]=1[CH:10]([O:11][CH3:12])[C:9]([NH:8][CH2:7][C:6]1[CH:5]=[CH:4][C:3]([C:1](=[NH:2])[NH:26][OH:27])=[CH:24][CH:23]=1)=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 21905122(RS)-N-(4-cyano-benzyl)-2-(2-fluoro-4-methoxy-phenyl)-2-methoxy-acetamide

Product 1

HCID 178491484HCID 178491484, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(RS)-N-(4-Cyano-benzyl)-2-(2-fluoro-4-methoxy-phenyl)-2-methoxy-acetamide (example 15.2, 251 mg) was dissolved in methanol (7 ml). Hydroxylamine hydrochloride (212 mg) and triethylamine (618 mg) were added. The mixture was stirred for 19 h at rt. The solvent was evaporated. The residue was dissolved in methylene chloride, washed with water, dried and filtered. The solvent was evaporated to give (RS)-2-(2-fluoro-4-methoxy-phenyl)-N-[4-(N-hydroxycarbamimidoyl)-benzyl]-2-methoxy-acetamide (269 mg) as an off-white foam. MS 362.2 ([M+H]+)

Workup

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in methylene chloride
  3. washwashed with water
  4. customdried
  5. filtrationfiltered
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-5d29362f77a54f3d94fd569f38f650da
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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