Hydrochloric Acid → HCID 22009041, compound

HRID 323331Notes

Reaction equation

HRID 323331 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:44]=[C:45]([O:49][CH3:50])[C:46]=1[O:47][CH3:48])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([NH:29][C:30]3[N:34]([CH2:35][C:36](=[O:39])[CH2:37][CH3:38])[C:33]4[CH:40]=[CH:41][CH:42]=[CH:43][C:32]=4[N:31]=3)[CH2:25][CH2:24]2)([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[C:15]([F:20])[CH:14]=2)[CH2:9]1)=[O:7].CO.[ClH:53]>C(OCC)C>[ClH:53].[CH3:50][O:49][C:45]1[CH:44]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:46]=1[O:47][CH3:48])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([NH:29][C:30]3[N:34]([CH2:35][C:36](=[O:39])[CH2:37][CH3:38])[C:33]4[CH:40]=[CH:41][CH:42]=[CH:43][C:32]=4[N:31]=3)[CH2:25][CH2:24]2)([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[C:15]([F:20])[CH:14]=2)[CH2:9]1)=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 9831448HCID 9831448, compound

Product 1

HCID 22009041HCID 22009041, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Combine 1-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1-(2-oxobutyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-difluorophenyl)pyrrolidine (1.38 g) and methanol (100 mL). Add a solution of hydrochloric acid (1.90 mL, 4 M in dioxane) and stir. After 18 hour, evaporate in vacuo to give a residue. Combine the residue and methanol (5 mL) and stir rapidly. Add diethyl ether (200 mL). After 2 hours, decant the solvent and add diethyl ether. After 18 hours, collect the solid and dry in vacuo at 65° C. to give the title compound: mp; 180-184° C.

Workup

  1. customevaporate in vacuo
  2. customto give a residue
  3. stirringstir rapidly
  4. waitAfter 2 hours
  5. customdecant the solvent
  6. additionadd diethyl ether
  7. waitAfter 18 hours
  8. customcollect the solid
  9. customdry in vacuo at 65° C.

Sources & evidence

ORD record
ord-a81a40d0ce684adc800ebf024e8344ad
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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