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Hydrochloric Acid → 1H-2-Benzazepine-4-acetic acid, 2,3,4,5-tetrahydro-3-oxo-8-[3-(2-pyridinylamino)propoxy]-2-(2,2,2-trifluoroethyl)-, (4S)-

HRID 2416741
Notes
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Reaction equation

HRID 2416741 reaction equation
[O:1]=[C:2]1[C@H:8]([CH2:9][C:10]([O:12]C)=[O:11])[CH2:7][C:6]2[CH:14]=[CH:15][C:16]([O:18][CH2:19][CH2:20][CH2:21][NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[CH:17][C:5]=2[CH2:4][N:3]1[CH2:29][C:30]([F:33])([F:32])[F:31].[OH-].[Na+].Cl>O1CCOCC1>[O:1]=[C:2]1[C@H:8]([CH2:9][C:10]([OH:12])=[O:11])[CH2:7][C:6]2[CH:14]=[CH:15][C:16]([O:18][CH2:19][CH2:20][CH2:21][NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[CH:17][C:5]=2[CH2:4][N:3]1[CH2:29][C:30]([F:33])([F:31])[F:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10695472HCID 10695472, compound

Product 1

HCID 99554611H-2-Benzazepine-4-acetic acid, 2,3,4,5-tetrahydro-3-oxo-8-[3-(2-pyridinylamino)propoxy]-2-(2,2,2-trifluoroethyl)-, (4S)-Yield 86.4%

Reagents, catalysts & solvents 1

HCID 312751,4-Dioxane
Solvent

Procedure

To a stirred solution of methyl (S)-3-oxo-8-[3-(pyridin-2-ylamino)-1-propyloxy]-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate (19.50 g, 42 mmol) in dioxane (150 mL) was added aqueous 1 N NaOH (75 mL, 75 mmol). The cloudy reaction was stirred at RT for 2 h, then the resulting homogeneous solution was neutralized with aqueous 1 N HCl (75 mL, 75 mmol). The solution was concentrated to near dryness by rotary evaporation to precipitate out the product. The supernatant was decanted off and the remaining gummy solid was redissolved in methanol. The clear solution was then reconcentrated by rotary evaporation. The remaining solid was triturated with a small volume of water, filtered and dried under vacuum to give the title compound (16.38 g, 86%) as a white powder. HPLC (Hamilton PRP-1®, 25% CH3CN/H2O containing 0.1% TFA) k′=3.1; [α]D−112.3° (c, 1.0, MeOH); MS (ES) m/e 452.3 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ 7.95 (dd, 1H), 7.34 (dt, 1H), 7.02 (d, J=9.2 Hz, 1H), 6.81 (m, 2H), 6.58 (t, 1H), 6.47 (m, 2H), 5.30 (d, J=16.5 Hz, 1H), 4.27-4.13 (m, 2H), 4.15 (d, J=16.5 Hz, 1H), 4.02 (t, 1H), 3.78 (m, 1H), 3.37 (m, 2H), 3.00 (dd, 1 H), 2.69 (dd, 1H), 2.65 (dd, 1H), 2.41 (dd, 1H), 1.96 (ddd, 2 H). Anal. Calcd for C22H24F3N3O4: C, 58.53; H, 5.36; N, 9.31. Found: C, 58.37; H, 5.42; N, 9.20.

Workup

  1. customThe cloudy reaction
  2. concentrationThe solution was concentrated
  3. customby rotary evaporation
  4. customto precipitate out the product
  5. customThe supernatant was decanted off
  6. dissolutionthe remaining gummy solid was redissolved in methanol
  7. customThe clear solution was then reconcentrated by rotary evaporation
  8. customThe remaining solid was triturated with a small volume of water
  9. filtrationfiltered
  10. customdried under vacuum

Sources & evidence

ORD record
ord-832f355a31914a7a98e16c5b200875f4
Source dataset
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06825188B2

Reaction notes

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