Hydroxyamine hydrochloride → HCID 141314901, compound

HRID 1948325Notes

Reaction equation

HRID 1948325 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:21]([CH:23]=O)[N:22]=2)[CH2:14][C@H:13]1[O:30][CH3:31])=[O:10].C([O-])(=O)C.[Na+].Cl.[NH2:38][OH:39]>C(O)C>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:21](/[CH:23]=[N:38]/[OH:39])[N:22]=2)[CH2:14][C@H:13]1[O:30][CH3:31])=[O:10]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 131730334HCID 131730334, compound

Product 1

HCID 141314901HCID 141314901, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of Cis(±)-ethyl 2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-formyl-1,3-thiazole -5-carboxylate (0.10 g, 0.2 mmol, Example 252), sodium acetate (0.041 g, 0.5 mmol) and hydroxylamine hydrochloride (0.028 g, 0.4 mmol) were heated to reflux in absolute ethanol for 3 hours. After cooling to room temperature the ethanol was removed under reduced pressure followed by EtOAc/H2O partitioning, drying with MgSO4 and concentrating to a yellow solid (0.081 g) MS (ES): 504 NMR: 1.25 (t, 3H) 1.75 (s, 2 H) 2.18 (s, 3 H) 3.31 (s, 3 H) 3.36 (s, 3 H) 3.55 (s, 1 H) 3.95 (s, 1 H) 4.18-4.26 (m, 2 H) 4.26 (d, 2 H) 7.16 (d, 1 H) 8.61 (s, 1 H) 11.72 (s, 1 H) 12.16 (s, 1 H).

Workup

  1. customwas removed under reduced pressure
  2. dry with materialdrying with MgSO4
  3. concentrationconcentrating to a yellow solid (0.081 g)

Sources & evidence

ORD record
ord-690c8678ba184394b49759212c04e837
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

Loading…