Triethylamine → HCID 178468073, compound

HRID 1247409Notes

Reaction equation

HRID 1247409 reaction equation
Cl.[NH2:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:14]=[C:13]([F:15])[C:12]([CH:16]([O:30][CH2:31][CH3:32])[C:17]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27](=[NH:29])[NH2:28])=[CH:23][CH:22]=3)=[O:18])=[C:11]([F:33])[CH:10]=2)=[CH:5][CH:4]=1.Cl.N[OH:36].C(N(CC)CC)C>CN(C=O)C>[NH2:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:14]=[C:13]([F:15])[C:12]([CH:16]([O:30][CH2:31][CH3:32])[C:17]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27](=[NH:28])[NH:29][OH:36])=[CH:23][CH:22]=3)=[O:18])=[C:11]([F:33])[CH:10]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 77702306HCID 77702306, compound

Product 1

HCID 178468073HCID 178468073, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (RS)-(2-[4-(6-amino-pyridin-3-yl)-2,6-difluoro-phenyl]-N-(4-carbamimidoyl-benzyl)-2-ethoxy-acetamide hydrochloride (example 271, 60 mg) in DMF (1 ml) were added hydroxylamine hydrochloride (27 mg) and triethylamine (38 mg). The mixture was stirred at 50° C. for 2.5 h. After cooling to rt, the mixture was partitioned between EtOAc and ice water and extracted with EtOAc. The organic phase was washed with water, dried, filtered and concentrated to give (RS)2-[4-(6-amino-pyridin-3-yl)-2,6-difluoro-phenyl]-2-ethoxy-N-[4-(N-hydroxycarbamimidoyl)-benzyl]-acetamide (57 mg). Colorless solid. MS 456.0 ([M+H]+)

Workup

  1. temperatureAfter cooling to rt
  2. customthe mixture was partitioned between EtOAc and ice water
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed with water
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1c60df71e729483881d8138d16fb55ef
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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