Methanol → HCID 88072162, compound

HRID 323313Notes

Reaction equation

HRID 323313 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:46]=[C:47]([O:51][CH3:52])[C:48]=1[O:49][CH3:50])[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]4[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=4)[C:33]4[CH:42]=[CH:43][CH:44]=[CH:45][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].[CH3:53][S:54]([OH:57])(=[O:56])=[O:55].CO.C(OCC)C>C(OCC)(=O)C>[CH3:53][S:54]([OH:57])(=[O:56])=[O:55].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:46]=[C:47]([O:51][CH3:52])[C:48]=1[O:49][CH3:50])[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]4[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=4)[C:33]4[CH:42]=[CH:43][CH:44]=[CH:45][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

6

Reactant 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 6395Methanesulfonic AcidHCID 9875019HCID 9875019, compound

Product 1

HCID 88072162HCID 88072162, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Combine 1-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1-(pyrid-2-ylmethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-difluorophenyl)pyrrolidine (1.1 g, 1.55 mmol) and ethyl acetate (90 mL). Add a solution of methanesulfonic acid (0.30 g, 3.01 mmol) in ethyl acetate (10 mL). Add methanol (20 mL) and heat to reflux. After 2 hours, evaporate in vacuo to give a residue. Combine the residue and diethyl ether (300 mL) and stir to form a solid. After 3 hours, decant the solvent, collect the solid, and dry to give the title compound.

Workup

  1. customevaporate in vacuo
  2. customto give a residue
  3. customto form a solid
  4. waitAfter 3 hours
  5. customdecant the solvent
  6. customcollect the solid
  7. customdry

Sources & evidence

ORD record
ord-c8eaf285aa754cd9a58c8d7da86455ff
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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