Hydrochloric Acid → HCID 178495117, compound

HRID 2065805Notes

Reaction equation

HRID 2065805 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:13][C:12]([C:14]([CH3:18])([CH3:17])[CH2:15][OH:16])=[N:11][C:10]=1[C:19]1[N:24]=[C:23]2[O:25][C:26]([NH:28][C@@H:29]([CH3:34])[CH2:30][CH2:31][O:32][CH3:33])=[N:27][C:22]2=[CH:21][CH:20]=1.[ClH:35].O1CCOCC1>C(OC)(C)(C)C>[ClH:35].[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:13][C:12]([C:14]([CH3:18])([CH3:17])[CH2:15][OH:16])=[N:11][C:10]=1[C:19]1[N:24]=[C:23]2[O:25][C:26]([NH:28][C@@H:29]([CH3:34])[CH2:30][CH2:31][O:32][CH3:33])=[N:27][C:22]2=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178495116HCID 178495116, compound

Product 1

HCID 178495117HCID 178495117, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
60 °C

Procedure

To a slightly pink suspension of 2-[5-(2,4-difluorophenyl)-4-[2-[[(1S)-3-methoxy-1-methyl-propyl]amino]oxazolo[5,4-b]pyridin-5-yl]-1H-imidazol-2-yl]-2-methyl-propan-1-ol (25.7 g, 54.51 mmol) in methyl tert-butyl ether (771 mL) at 60° C., is added a 4.0 M HCl solution in dioxane (16.35 mL, 65.41 mmol). The resulting suspension is heated to 60° C. for 30 min and then allowed to reach RT gradually. A solid is formed and is filtered under an inert atmosphere of nitrogen and quickly collected and dried under vacuum at 60° C. overnight to provide the title compound as a creamy solid (27 g, 98%). LC-ES/MS m/z 472 (M+1).

Workup

  1. customto reach RT
  2. customA solid is formed
  3. filtrationis filtered under an inert atmosphere of nitrogen
  4. customquickly collected
  5. customdried under vacuum at 60° C. overnight

Sources & evidence

ORD record
ord-ea2eae08c7774a04b46f3ba13ca1769b
Source dataset
uspto-grants-2012_10
Patent number
US08288548B2

Reaction notes

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