Sodium Carbonate → N'-Hydroxy-2-{3-[2-(trifluoromethyl)phenoxy]pyrrolidin-1-yl}-1,3-thiazole-5-carboximidamide

HRID 2355062Notes

Reaction equation

HRID 2355062 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=1[O:5][CH:6]1[CH2:10][CH2:9][N:8]([C:11]2[S:12][C:13]([C:16]#[N:17])=[CH:14][N:15]=2)[CH2:7]1.Cl.[NH2:25][OH:26].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O>[OH:26][N:25]=[C:16]([C:13]1[S:12][C:11]([N:8]2[CH2:9][CH2:10][CH:6]([O:5][C:4]3[CH:18]=[CH:19][CH:20]=[CH:21][C:3]=3[C:2]([F:23])([F:1])[F:22])[CH2:7]2)=[N:15][CH:14]=1)[NH2:17]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 684535482-{3-[2-(Trifluoromethyl)phenoxy]pyrrolidin-1-yl}-1,3-thiazole-5-carbonitrile

Product 1

HCID 86629248N'-Hydroxy-2-{3-[2-(trifluoromethyl)phenoxy]pyrrolidin-1-yl}-1,3-thiazole-5-carboximidamide

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-{3-[2-(trifluoromethyl)phenoxy]pyrrolidin-1-yl}-1,3-thiazole-5-carbonitrile (370 mg, 1.1 mmol), hydroxylamine hydrochloride (303 mg, 4.4 mmol) and sodium carbonate (231 mg, 2.2 mmol) in EtOH—H2O (4:1, 20 mL) was heated at 80° C. for 2 h. Solvent was evaporated in vacuo. The residue was diluted with H2O, extracted three times with EtOAc, dried (Na2SO4) and concentrated. Trituration with hexanes:Et2O (1:1) gave the title compound as white powder. 1H NMR (400 MHz, acetone-d6): δ 8.73 (s, 1 H), 7.66 (m, 2 H), 7.52 (s, 1 H), 7.38 (d, 1 H), 7.16 (t, 1 H), 5.46 (m, 3 H), 3.94-3.88 (m, 1 H), 3.75-3.59 (m, 3 H), 2.56-2.30 (m, 2 H).

Workup

  1. customSolvent was evaporated in vacuo
  2. additionThe residue was diluted with H2O
  3. extractionextracted three times with EtOAc
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-15b49b863db84f06a30a9588e801531f
Source dataset
uspto-grants-2010_07
Patent number
US07754745B2

Reaction notes

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