HCID 86662263, compound → HCID 66740747, compound

HRID 1627403Notes

Reaction equation

HRID 1627403 reaction equation
[N:1]([C:4]1[N:5]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[C:6]([C:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([O:19][CH3:20])[CH:13]=2)([CH3:11])[CH3:10])=[CH:7][N:8]=1)=[N+]=[N-]>CO.C1COCC1>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C:9]([C:6]2[N:5]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[C:4]([NH2:1])=[N:8][CH:7]=2)([CH3:11])[CH3:10])=[CH:13][C:14]=1[O:19][CH3:20]

Participants

3

Reactant 1

HCID 86662263HCID 86662263, compound

Product 1

HCID 66740747HCID 66740747, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of 2-azido-5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole (0.126 g, 0.33 mmol) was added MeOH-THF (3 mL, 1:1, v/v) was sparged with argon briefly. Next 5% Pd on CaCO3 poisoned with lead was added to the flask, which then was purged with hydrogen and stirred under 1 atm hydrogen. After 3 h, when the reaction was shown to be complete by LCMS, the mixture was filtered through Celite™ and concentrated in vacuo to afford 5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-amine (93 mg) as a beige solid. MS (EI) m/z 360 [M+H]+.

Workup

  1. customv/v) was sparged with argon briefly
  2. additionwas added to the flask, which
  3. customthen was purged with hydrogen
  4. filtrationthe mixture was filtered through Celite™
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-27310561a646423a91915bf7a59397c9
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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