Dimethylformamide → Trelanserin

HRID 549784Notes

Reaction equation

HRID 549784 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][N:18]([C:21]4[C:26]5[CH:27]=[CH:28][S:29][C:25]=5[CH:24]=[CH:23][N:22]=4)[CH2:17][CH2:16]3)=[CH:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.Cl[CH2:31][C:32]([NH2:34])=[O:33].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][N:18]([C:21]4[C:26]5[CH:27]=[CH:28][S:29][C:25]=5[CH:24]=[CH:23][N:22]=4)[CH2:17][CH2:16]3)=[CH:7][C:8](=[O:12])[N:9]2[CH2:31][C:32]([NH2:34])=[O:33])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6580ChloroacetamideHCID 11430Potassium CarbonateHCID 15859997HCID 15859997, compound

Product 1

HCID 9869105Trelanserin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

66.9 kg of 7-fluoro-4-[2-[4-[thieno[3,2-c]pyridin-4-yl]piperazin-1-yl]ethyl]-quinolin-2(1H)-one (V), 18.4 kg of 2-chloroacetamide (1.2 eq.), 51.5 kg of potassium carbonate (2 eq.) and 335 l of DMF are introduced into a reactor. The mixture is stirred at 50° C. for twenty hours and then cooled to 25° C. and 1000 l of water are added. The suspension obtained is filtered and washed with water and a paste is re-formed in 307 l of ethanol. The solid is filtered off. 60.7 kg, estimated on a dry basis, of a white solid (II) are obtained.

Workup

  1. temperaturecooled to 25° C.
  2. customThe suspension obtained
  3. filtrationis filtered
  4. washwashed with water
  5. customa paste is re-formed in 307 l of ethanol
  6. filtrationThe solid is filtered off
  7. customare obtained

Sources & evidence

ORD record
ord-b882a7f758d5442c86fa6c5822359bdd
Source dataset
uspto-grants-2011_05
Patent number
US07943769B2

Reaction notes

Loading…