Diethyl Ether → N-(5-(3,4-Difluorobenzylcarbamoyl)-2-fluorophenyl)-7-(3-hydroxy-3-methyl butyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 335287Notes

Reaction equation

HRID 335287 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][C:37]=1[F:38])[CH2:5][NH:6][C:7]([C:9]1[CH:10]=[CH:11][C:12]([F:34])=[C:13]([NH:15][C:16]([C:18]2[N:22]3[CH:23]=[CH:24][C:25]([CH2:27][CH2:28]C(OCC)=O)=[CH:26][C:21]3=[N:20][CH:19]=2)=[O:17])[CH:14]=1)=[O:8].[CH3:39][Mg]Br.CC[O:44][CH2:45][CH3:46]>>[F:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][C:37]=1[F:38])[CH2:5][NH:6][C:7]([C:9]1[CH:10]=[CH:11][C:12]([F:34])=[C:13]([NH:15][C:16]([C:18]2[N:22]3[CH:23]=[CH:24][C:25]([CH2:27][CH2:28][C:45]([OH:44])([CH3:46])[CH3:39])=[CH:26][C:21]3=[N:20][CH:19]=2)=[O:17])[CH:14]=1)=[O:8]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 71283043Ethyl 3-(3-(5-(3,4-difluorobenzylcarbamoyl)-2-fluorophenylcarbamoyl)imidazo[1,2-a]pyridin-7-yl)propanoateHCID 178418573HCID 178418573, compound

Product 1

HCID 71282999N-(5-(3,4-Difluorobenzylcarbamoyl)-2-fluorophenyl)-7-(3-hydroxy-3-methyl butyl)imidazo[1,2-a]pyridine-3-carboxamide

Conditions

Temperature
0 °C

Procedure

Ethyl 3-(3-(5-(3,4-difluorobenzylcarbamoyl)-2-fluorophenylcarbamoyl)imidazo[1,2-a]pyridin-7-yl)propanoate (step 1) (50 mg, 0.095 mmol) was suspended in dry ether and cooled to 0° C. Methylmagnesium bromide (0.318 ml, 3.0M in ether, 0.953 mmol) was added and the mixture was stirred and allowed to warm to RT over 16 hrs. The mixture was partitioned between 10% aq. Citric acid and EtOAc. The organics were separated, dried (MgSO4), filtered and evaporated to dryness. The residue was purified by chromatography on silica eluting with 0-10% MeOH in DCM to afford the title product;

Workup

  1. temperatureto warm to RT over 16 hrs
  2. customThe mixture was partitioned between 10% aq. Citric acid and EtOAc
  3. customThe organics were separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by chromatography on silica eluting with 0-10% MeOH in DCM

Sources & evidence

ORD record
ord-9146f4f6d50d4074b8b716b47c2874be
Source dataset
uspto-grants-2014_11
Patent number
US08883819B2

Reaction notes

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