Sodium Hydroxide → HCID 44128985, compound

HRID 1514277Notes

Reaction equation

HRID 1514277 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:8]=[C:7]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:30]=[CH:29][C:17]4[CH2:18][CH2:19][N:20]([CH2:23][C:24]([O:26]CC)=[O:25])[CH2:21][CH2:22][C:16]=4[CH:15]=3)[N:10]=2)[CH:6]=[CH:5][C:4]=1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[OH-].[Na+]>C(O)C>[F:38][C:2]([F:1])([F:37])[C:3]1[CH:8]=[C:7]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:30]=[CH:29][C:17]4[CH2:18][CH2:19][N:20]([CH2:23][C:24]([OH:26])=[O:25])[CH2:21][CH2:22][C:16]=4[CH:15]=3)[N:10]=2)[CH:6]=[CH:5][C:4]=1[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59403448HCID 59403448, compound

Product 1

HCID 44128985HCID 44128985, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of ethyl (7-{5-[2-(trifluoromethyl)-4-biphenylyl]-1,2,4-oxadiazol-3-yl}-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)acetate (Preparation 49) (22 mg, 0.04 mmol), aqueous sodium hydroxide (2M, 220 μL, 0.44 mmol) and ethanol (2.2 ml) was heated at 40° C. for 1 h. The reaction mixture was cooled to room temperature and concentrated. The residue was taken up in water, which was then acidified to pH 6 with acetic acid. The aqueous phase was extracted with EtOAc (2×20 ml) before the combined organic fractions were concentrated and the residue was triturated with EtOAc and the title compound was filtered off and dried in a vacuum oven to give a white solid (13 mg, 0.03 mmol). δH (d6DMSO, 400 MHz): 8.52 (1H, d), 8.50 (1H, dd), 7.92-7.86 (2H, m), 7.73 (1H, d), 7.54-7.49 (3H, m), 7.44-7.35 (3H, m), 3.18 (2H, s), 3.05-2.96 (4H, m), 2.85-2.79 (4H, m); MS (ES−): C27H22F3N3O3 requires 493; found 492 [M−H+].

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. extractionThe aqueous phase was extracted with EtOAc (2×20 ml) before the combined organic fractions
  4. concentrationwere concentrated
  5. customthe residue was triturated with EtOAc
  6. filtrationthe title compound was filtered off
  7. customdried in a vacuum oven

Sources & evidence

ORD record
ord-d4a36fd8b26e42cfbcf21dc468290e22
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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