Sodium Hydroxide → BI 207127

HRID 1907894Notes

Reaction equation

HRID 1907894 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[N:9]([CH3:48])[C:10]3[C:15]([C:16]=2[CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:14][CH:13]=[C:12]([C:22]([NH:24][C:25]2([C:29]4[N:33]([CH3:34])[C:32]5[CH:35]=[C:36](/[CH:39]=[CH:40]/[C:41]([O:43]CCCC)=[O:42])[CH:37]=[CH:38][C:31]=5[N:30]=4)[CH2:28][CH2:27][CH2:26]2)=[O:23])[CH:11]=3)=[N:6][CH:7]=1.C1COCC1.CO.[OH-].[Na+].[Na]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[N:9]([CH3:48])[C:10]3[C:15]([C:16]=2[CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)=[CH:14][CH:13]=[C:12]([C:22]([NH:24][C:25]2([C:29]4[N:33]([CH3:34])[C:32]5[CH:35]=[C:36](/[CH:39]=[CH:40]/[C:41]([OH:43])=[O:42])[CH:37]=[CH:38][C:31]=5[N:30]=4)[CH2:26][CH2:27][CH2:28]2)=[O:23])[CH:11]=3)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 5360545SodiumHCID 21899815MeOH tetrahydrofuranHCID 86665161HCID 86665161, compound

Product 1

HCID 56948249BI 207127

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In this process, hydrolysis of (E)-butyl 3-(2-(1-(2-(5-bromopyrimidin-2-yl)-3-cyclopentyl-1-methyl-1H-indole-6-carboxamido)cyclobutyl)-1-methyl-1H-benzo[d]imidazol-6-yl)acrylate was carried out in mixture of THF/MeOH and aq NaOH. Controlled acidification of the corresponding sodium salt with acetic acid is very critical to obtain easy-filtering crystalline product in high yield and purity.

Workup

  1. customto obtain
  2. filtrationeasy-filtering crystalline product
  3. customin high yield

Sources & evidence

ORD record
ord-411256c57407476b9048850da7da7fc3
Source dataset
uspto-grants-2013_12
Patent number
US08598183B2

Reaction notes

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