Water → HCID 15859997, compound

HRID 549783Notes

Reaction equation

HRID 549783 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH2:13][C:14]([N:16]3[CH2:21][CH2:20][N:19]([C:22]4[C:27]5[CH:28]=[CH:29][S:30][C:26]=5[CH:25]=[CH:24][N:23]=4)[CH2:18][CH2:17]3)=O)=[CH:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH2:13][CH2:14][N:16]3[CH2:21][CH2:20][N:19]([C:22]4[C:27]5[CH:28]=[CH:29][S:30][C:26]=5[CH:25]=[CH:24][N:23]=4)[CH2:18][CH2:17]3)=[CH:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 25028976HCID 25028976, compound

Product 1

HCID 15859997HCID 15859997, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

107.7 kg (1 eq.) of intermediate 7-fluoro-4-[2-[4-(thieno[3,2-c]pyridin-4-yl)piperazin-1-yl]-2-oxoethyl]quinolin-2(1H)-one (I), followed by 3231 of THF, are introduced, in thirty minutes at 10° C., into a suspension of 22.2 kg (2.3 eq.) of lithium aluminium hydride in 580 l of tetrahydrofuran, in a reactor. The mixture is stirred for three hours at ambient temperature and then, after verification that the reaction is complete, the mixture is cooled and 21.5 l of water, 21.5 l of 4N sodium hydroxide and 180 l of water are added successively without the temperature exceeding 15° C. The mixture is stirred for one hour and the inorganic salts are filtered off. The mixture is concentrated to three volumes of THF and run into 1400 l of water. The mixture is filtered and a paste is re-formed in 1000 l of a water/THF mixture: 3/7. The product is dried under vacuum at 50° C. Compound (V) is obtained.

Workup

  1. temperaturethe mixture is cooled
  2. customexceeding 15° C
  3. stirringThe mixture is stirred for one hour
  4. filtrationthe inorganic salts are filtered off
  5. concentrationThe mixture is concentrated to three volumes of THF
  6. filtrationThe mixture is filtered
  7. customa paste is re-formed in 1000 l of a water/THF mixture
  8. customThe product is dried under vacuum at 50° C

Sources & evidence

ORD record
ord-8a4f2e7d28484de284e89c28b49d7f29
Source dataset
uspto-grants-2011_05
Patent number
US07943769B2

Reaction notes

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