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Sodium Hydroxide → 2-amino-5-[4-(difluoromethoxy)phenyl]-3-methyl-5-[3-(pyrrolidin-1-ylmethyl)phenyl]-3,5-dihydro-4H-imidazol-4-one

HRID 2240976
Notes
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Reaction equation

HRID 2240976 reaction equation
[NH2:1][C:2]1[N:3]([CH3:26])[C:4](=[O:25])[C:5]([C:17]2[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=2)[CH:20]=O)([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH:14]([F:16])[F:15])=[CH:9][CH:8]=2)[N:6]=1.[NH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCCl.C(O)(=O)C>[NH2:1][C:2]1[N:3]([CH3:26])[C:4](=[O:25])[C:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH:14]([F:15])[F:16])=[CH:9][CH:8]=2)([C:17]2[CH:24]=[CH:23][CH:22]=[C:19]([CH2:20][N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[CH:18]=2)[N:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 16113437HCID 16113437, compound

Product 1

HCID 251282662-amino-5-[4-(difluoromethoxy)phenyl]-3-methyl-5-[3-(pyrrolidin-1-ylmethyl)phenyl]-3,5-dihydro-4H-imidazol-4-oneYield 82.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolvent2×

Procedure

A small vial (10 ml) was charged with 3-[2-Amino-4-(4-difluoromethoxy-phenyl)-1-methyl-5-oxo-4,5-dihydro-1H-imidazol-4-yl]-benzaldehyde (69 mg, 192 μmol) and 1,2-dichloroethane (DCE, 1 ml). To this was added one-third of a solution of pyrrolidine (41 mg, 0.576 mmol) in 1,2-dichloroethane (3.00 ml). After stirring overnight at room temperature sodium triacetoxyborohydride (58 mg, 270 μmol) was added followed by 1 drop of glacial acetic acid (˜12 mg), then after another 20 hours 1N sodium hydroxide (1 ml) was added and the mixture extracted with diethyl ether. The ethereal layer was concentrated by rotary evaporation, diluted with methanol and re-concentrated (repeated three times). Finally the oily residue was redissolved in diethylether/hexanes and concentrated, twice then placed under vacuum to give a white foam 66 mg (82%) 1H NMR (400 MHz, DMSO-d6) δ ppm 1.61 (t, J=3.4 Hz, 4H) 2.32 (t, J=6.5 Hz, 4H) 2.93 (s, 3H) 3.44 (s, 2H) 6.62 (br. s., 3H) 7.05 (d, J=8.8 Hz, 2H) 7.08-7.11 (m, 1H) 7.12 (t, J=74.18 Hz, 1H) 7.17 (t, J=7.6 Hz, 1H) 7.25 (t, J=4.6 Hz, 1H) 7.34 (s, 1H) 7.40 (d, J=8.8 Hz, 2H); MS (ES) m/z 413.3 [M−H]−

Workup

  1. additionwas added
  2. extractionthe mixture extracted with diethyl ether
  3. concentrationThe ethereal layer was concentrated by rotary evaporation
  4. additiondiluted with methanol
  5. concentrationre-concentrated (repeated three times)
  6. dissolutionFinally the oily residue was redissolved in diethylether/hexanes
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5a5255fa648b45ee8160284192603a42
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07723368B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes