Hydrochloric Acid → 2-(6-(4-Cyclopentyl-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazol-3-yl)acetic Acid

HRID 515677Notes

Reaction equation

HRID 515677 reaction equation
[CH:1]1([C:6]2[CH:31]=[CH:30][C:9]([CH2:10][O:11][C:12]3[CH:13]=[CH:14][C:15]4[N:19]5[CH2:20][CH2:21][CH:22]([CH2:23][C:24]([O:26]CC)=[O:25])[C:18]5=[N:17][C:16]=4[CH:29]=3)=[CH:8][C:7]=2[C:32]([F:35])([F:34])[F:33])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Li+].Cl>O1CCOCC1>[CH:1]1([C:6]2[CH:31]=[CH:30][C:9]([CH2:10][O:11][C:12]3[CH:13]=[CH:14][C:15]4[N:19]5[CH2:20][CH2:21][CH:22]([CH2:23][C:24]([OH:26])=[O:25])[C:18]5=[N:17][C:16]=4[CH:29]=3)=[CH:8][C:7]=2[C:32]([F:34])([F:35])[F:33])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67248467Ethyl 2-(6-(4-Cyclopentyl-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazol-3-yl)acetate

Product 1

HCID 583295932-(6-(4-Cyclopentyl-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazol-3-yl)acetic AcidYield 100.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl 2-(6-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazol-3-yl)acetate (0.109 g, 0.224 mmol) was dissolved in dioxane (2.5 mL) and 1.0 M aqueous lithium hydroxide (0.672 mL, 0.672 mmol) was added. The reaction mixture was stirred at room temperature for 1.5 h and then acidified (pH 2) with 1.0 M HCl. The reaction mixture was extracted three times with EtOAc and the combined extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure to provide the title compound (103 mg). LCMS m/z=459.3 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.54-1.65 (m, 2H), 1.67-1.79 (m, 2H), 1.80-1.91 (m, 2H), 2.05-2.14 (m, 2H), 2.42-2.53 (m, 1H), 2.89 (d, J=7.1 Hz, 1H), 2.95-3.22 (m, 2H), 3.33-3.43 (m, 1H), 3.78-3.87 (m, 1H), 4.03-4.12 (m, 1H), 4.14-4.23 (m, 1H), 5.09 (s, 2H), 6.88 (d, J=2.4 Hz, 1H), 6.97 (dd, J=8.8, 2.5 Hz, 1H), 7.48 (d, J=8.2 Hz, 1H), 7.57 (d, J=8.1 Hz, 1H), 7.62 (d, J=8.8 Hz, 1H), 7.68 (s, 1H).

Workup

  1. extractionThe reaction mixture was extracted three times with EtOAc
  2. dry with materialthe combined extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6727251fe1cd4cdd93cd689b577ee07b
Source dataset
uspto-grants-2015_08
Patent number
US09108969B2

Reaction notes

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