Lithium Hydroxide → HCID 9911639, compound

HRID 2416720Notes

Reaction equation

HRID 2416720 reaction equation
[Li+].[OH-].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:35]=[CH:34][C:17]2[CH2:18][CH:19]([CH2:29][C:30]([O:32]C)=[O:31])[C:20](=[O:28])[N:21]([CH2:23][C:24]([F:27])([F:26])[F:25])[CH2:22][C:16]=2[CH:15]=1>C1COCC1.O>[O:28]=[C:20]1[CH:19]([CH2:29][C:30]([OH:32])=[O:31])[CH2:18][C:17]2[CH:34]=[CH:35][C:14]([O:13][CH2:12][CH2:11][CH2:10][NH:9][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=3)=[CH:15][C:16]=2[CH2:22][N:21]1[CH2:23][C:24]([F:27])([F:25])[F:26]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 54558526HCID 54558526, compound

Product 1

HCID 9911639HCID 9911639, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.0 N LiOH (0.44 mL, 0.44 mmole) was added to a solution of methyl (±)-8-[3-(2-pyridylamino)-1-propyloxy]-3-oxo-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate (159.5 mg, 0.34 mmole) in THF (1.7 mL) and H2O (1.3 mL) at RT. The yellow, cloudy reaction became homogeneous within 10 min. After 24 hr, the reaction was concentrated to dryness and the yellow residue was dissolved in H2O (4 mL). The solution was filtered, then was carefully neutralized (pH≈7) with 1.0 N HCl. The precipitate was collected, washed with plenty of H2O, and dried in high vacuum at 40-45° C. to afford the title compound (130.0 mg, 83%) as an off-white solid: HPLC (PRP-1®, 25% CH3CN/H2O containing 0.1% TFA) k′=3.1; 1H NMR (400 MHz, DMSO-d6) δ 7.91-8.00 (m, 1 H), 7.28-7.40 (m, 1 H), 7.02 (d, J=9.2 Hz, 1 H), 6.76-6.87 (m, 2 H), 6.51-6.02 (m, 1 H), 6.39-6.50 (m, 2 H), 5.30 (d, J=16.6 Hz, 1 H), 4.10-4.30 (m, 3 H), 4.02(t, J=6.3 Hz, 1 H), 3.70-3.82 (m, 1 H), 3.20-3.45 (m, 2 H, partially obscured by residual solvent signal), 2.99 (dd, 1 H), 2.59-2.74 (m, 2 H), 2.39 (dd, J=16.9, 4.8 Hz, 1 H), 1.90-2.03 (m, 2 H); MS (ES) m/e 452 (M+H)+. Anal. Calcd for C22H24F3N3O4.0.5 H2O: C, 57.39; H. 5.47; N, 9.13. Found: C, 57.39; H, 5.18; N, 9.00.

Workup

  1. customThe yellow, cloudy reaction
  2. waitAfter 24 hr
  3. concentrationthe reaction was concentrated to dryness
  4. dissolutionthe yellow residue was dissolved in H2O (4 mL)
  5. filtrationThe solution was filtered
  6. customThe precipitate was collected
  7. washwashed with plenty of H2O
  8. customdried in high vacuum at 40-45° C.

Sources & evidence

ORD record
ord-f36028ac65f342a38d26fbd80a3499ef
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

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