Hydrochloric Acid → HCID 178479722, compound

HRID 518606Notes

Reaction equation

HRID 518606 reaction equation
[F:1][C:2]1[CH:36]=[CH:35][C:5]([C:6]([NH:8][C:9]2[N:13]([C@@H:14]3[CH2:19][CH2:18][C@H:17]([C:20]([O:22]C)=[O:21])[CH2:16][CH2:15]3)[C:12]3[CH:24]=[C:25]([CH2:28][N:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)[CH:26]=[CH:27][C:11]=3[N:10]=2)=[O:7])=[CH:4][CH:3]=1.CO.[OH-].[Na+].[ClH:41]>CCOCC>[ClH:41].[F:1][C:2]1[CH:36]=[CH:35][C:5]([C:6]([NH:8][C:9]2[N:13]([C@@H:14]3[CH2:19][CH2:18][C@H:17]([C:20]([OH:22])=[O:21])[CH2:16][CH2:15]3)[C:12]3[CH:24]=[C:25]([CH2:28][N:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)[CH:26]=[CH:27][C:11]=3[N:10]=2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 178501178HCID 178501178, compound

Product 1

HCID 178479722HCID 178479722, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A round bottom flask under nitrogen atmosphere was charged with cis-methyl 4-(2-(4-fluorobenzamido)-6-(piperidin-1-ylmethyl)-1H-benzo[d]imidazol-1-yl)cyclohexanecarboxylate (0.10 g, 0.203 mmol), MeOH (2.90 mL) and 1N aqueous NaOH (3.05 mL, 3.05 mmol) and stirred at RT overnight. The reaction mixture was adjusted to a pH of approximately 2 by treatment with 6N HCl and was extracted with DCM (3×50 mL). The organic layers were combined, dried over sodium sulfate and concentrated under vacuum to afford an off-white solid. Trituration with ether afforded cis-4-(2-(4-fluorobenzamido)-6-(piperidin-1-ylmethyl)-1H-benzo[d]imidazol-1-yl)cyclohexanecarboxylic acid hydrochloride as a white solid (0.095 g, 91% yield). MS m/z=479.2 [M+H]. Calc'd for C27H31N4O3: 478.2.

Workup

  1. extractionwas extracted with DCM (3×50 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customto afford an off-white solid

Sources & evidence

ORD record
ord-29d9f9bf2055436ab2967abc15adc90d
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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