Hydrochloric Acid → HCID 86761214, compound

HRID 1174057Notes

Reaction equation

HRID 1174057 reaction equation
C([O:4][CH2:5][CH2:6][N:7]1[C:12](=[O:13])[CH2:11][N:10]2[CH:14]([C:35](=[CH2:38])[CH2:36][CH3:37])[C:15]3([C:32]4[C:27](=[CH:28][C:29]([Cl:33])=[CH:30][CH:31]=4)[NH:26][C:25]3=[O:34])[CH:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=3)[CH2:17][C:9]2=[N:8]1)(=O)C.[OH-].[Na+].Cl>O1CCCC1.CO>[Cl:33][C:29]1[CH:28]=[C:27]2[NH:26][C:25](=[O:34])[C:15]3([CH:14]([C:35](=[CH2:38])[CH2:36][CH3:37])[N:10]4[C:9](=[N:8][N:7]([CH2:6][CH2:5][OH:4])[C:12](=[O:13])[CH2:11]4)[CH2:17][CH:16]3[C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=3)[C:32]2=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86761215HCID 86761215, compound

Product 1

HCID 86761214HCID 86761214, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of racemic (6′R, 3R, 8′S)-2′-(2-acetoxyethyl)-6-chloro-8′-(3-chlorophenyl)-6′-(1-methylene-propyl)-6′,7′,8′,9′-tetrahydro spiro[3H-indole-3,7′-(2H-pyrido[2,1-c][1,2,4]triazine)]-2,3′(1H)-dione (0.3 g, 0.54 mmol) prepared in example 7b in tetrahydrofuran (25 mL) and methanol (15 mL) was added sodium hydroxide aqueous solution (1N, 10 mL). the reaction mixture was stirred at room temperature for 2 h, then neutralized to “pH” 7 by aqueous HCl. The mixture was then extracted with ethyl acetate. The organic layer was separated, died over MgSO4, concentrated, and dried in vacuo to give racemic racemic (6′R, 3R, 8′S)-6-chloro-8′-(3-chlorophenyl)-2′-(2-hydroxyethyl)-6′-(1-methylene-propyl)-6′,7′,8′,9′-tetrahydro spiro[3H-indole-3,7′-(2H-pyrido[2,1-c][1,2,4]triazine)]-2,3′(1H)-dione as a white solid (0.22 g, 79%)

Workup

  1. extractionThe mixture was then extracted with ethyl acetate
  2. customThe organic layer was separated
  3. concentrationconcentrated
  4. customdried in vacuo

Sources & evidence

ORD record
ord-a5971fac04484a25b78b977647ad893a
Source dataset
uspto-grants-2010_11
Patent number
US07834179B2

Reaction notes

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