Triethylamine → HCID 86612741, compound

HRID 602999Notes

Reaction equation

HRID 602999 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH:14]2[CH2:17][N:16]([C@@H:18]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)[C:19]3[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=3)[C:22]#[N:23])[CH2:15]2)[C:10]([F:13])([CH3:12])[CH3:11])[CH:5]=[C:6]([F:8])[CH:7]=1.Cl.[NH2:35][OH:36].C(N(CC)CC)C>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH:14]2[CH2:17][N:16]([C@@H:18]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)[C:19]3[CH:20]=[C:21]([C:22](=[N:35][OH:36])[NH2:23])[CH:24]=[CH:25][CH:26]=3)[CH2:15]2)[C:10]([F:13])([CH3:12])[CH3:11])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 67055313HCID 67055313, compound

Product 1

HCID 86612741HCID 86612741, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 240 mg (0.45 mmol) of 3-[(S)-{3-[(1S)-1-(3-bromo-5-fluorophenyl)-2-fluoro-2-methylpropyl]azetidin-1-yl}(4-chlorophenyl)methyl]benzonitrile, 47.2 mg (0.68 mmol) of hydroxylamine hydrochloride, 0.124 mL (0.9 mmol) of triethylamine, and 5 mL of ethanol was heated to reflux for 4 h. The solution was concentrated and the residue was poured into 20 mL of CH2Cl2 and 5 mL of aq NaHCO3 (PH>7). The aqueous layer was extracted with two 10 mL portions of CH2Cl2. The combined organic layer was dried over Na2SO4 and concentrated to afford the title compound as a white solid; Mass Spectrum: m/e=562 (M+1, 35Cl), 564 (M+1, 37Cl).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. concentrationThe solution was concentrated
  4. additionthe residue was poured into 20 mL of CH2Cl2 and 5 mL of aq NaHCO3 (PH>7)
  5. extractionThe aqueous layer was extracted with two 10 mL portions of CH2Cl2
  6. dry with materialThe combined organic layer was dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-dc7ceb5b214a457e81e0cc12f575e320
Source dataset
uspto-grants-2011_03
Patent number
US07906652B2

Reaction notes

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