Methanol → HCID 178525539, compound

HRID 2378705Notes

Reaction equation

HRID 2378705 reaction equation
[Cl:1][C:2]1[C:10]2[C:9]3[CH2:11][N:12]([CH2:22][CH2:23][N:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)[C:13](=[O:21])[C@H:14]([CH2:16][C:17]([O:19]C)=[O:18])[CH2:15][C:8]=3[CH:7]=[C:6]([Cl:30])[C:5]=2[NH:4][N:3]=1.O1CCCC1.CO.O.O.[OH-].[Li+]>>[Cl:1][C:2]1[C:10]2[C:9]3[CH2:11][N:12]([CH2:22][CH2:23][N:24]4[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]4)[C:13](=[O:21])[C@H:14]([CH2:16][C:17]([OH:19])=[O:18])[CH2:15][C:8]=3[CH:7]=[C:6]([Cl:30])[C:5]=2[NH:4][N:3]=1

Participants

6

Reactant 5

HCID 887MethanolHCID 962WaterHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 178500649HCID 178500649, compound

Product 1

HCID 178525539HCID 178525539, compoundYield 50%

Conditions

Temperature
50 °C

Procedure

(S)-Methyl 2-(1,4-dichloro-8-oxo-9-(2-(piperidin-1-yl)ethyl)-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-yl)acetate (260 mg, 0.573 mmol) was dissolved in a mixture of tetrahydrofuran (5.0 mL, 61.6 mmol) and methanol (5.0 mL, 123 mmol). Water (5.0 mL, 278 mmol) was added to the mixture followed by lithium hydroxide hydrate (65 mg, 1.549 mmol). Mixture was warmed to 50° C. and held with stirring for 4.5 hours. Mixture was cooled to room temperature. Organic solvents were removed from the mixture by roto-vap. Residue was neutralized with 1.6 mL 1N hydrochloric acid and treated with ethyl acetate. Mixture sat at room temperature for 20 minutes allowing solids to form. Solids were filtered off and washed with water. Solids were dried in vacuo. Title compound was obtained as white solid in 50% yield. MS (M−H)−=437.1, 439.2.

Workup

  1. temperatureMixture was cooled to room temperature
  2. customOrganic solvents were removed from the mixture by roto-vap
  3. additiontreated with ethyl acetate
  4. waitMixture sat at room temperature for 20 minutes
  5. customto form
  6. filtrationSolids were filtered off
  7. washwashed with water
  8. customSolids were dried in vacuo

Sources & evidence

ORD record
ord-36067788178b492c828be8dadc4d4885
Source dataset
uspto-grants-2008_12
Patent number
US07470679B2

Reaction notes

Loading…