Imidazole → HCID 70656209, compound

HRID 872685Notes

Reaction equation

HRID 872685 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.[Cl:8][C:9]1[CH:10]=[C:11]([C:17]2[CH:21]=[CH:20][N:19]([CH2:22][C@@H:23]([NH:25][C:26]([C:28]3[N:29]=[C:30]([CH2:33]Cl)[O:31][CH:32]=3)=[O:27])[CH3:24])[N:18]=2)[CH:12]=[CH:13][C:14]=1[C:15]#[N:16]>CN(C=O)C>[N:3]1([CH2:33][C:30]2[O:31][CH:32]=[C:28]([C:26]([NH:25][CH:23]([CH3:24])[CH2:22][N:19]3[CH:20]=[CH:21][C:17]([C:11]4[CH:12]=[CH:13][C:14]([C:15]#[N:16])=[C:9]([Cl:8])[CH:10]=4)=[N:18]3)=[O:27])[N:29]=2)[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 70656906HCID 70656906, compound

Product 1

HCID 70656209HCID 70656209, compoundYield 8.23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

Sodium hydride (11.87 mg, 0.297 mmol) was added into a flask under nitrogen atmosphere. The flask was cooled to 0° C. and DMF was added through a septum. Imidazole (13.47 mg, 0.198 mmol) was added and the mixture was stirred for 60 min in RT. The mixture was again cooled to 0° C. and (S)—N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-2-(chloromethyl)oxazole-4-carboxamide (80 mg, 0.198 mmol) in DMF was added dropwise. The reaction mixture was stirred overnight in RT. DMF was evaporated and the resulting crude product was dissolved in DCM, washed with brine and evaporated. The product was triturated using diethyl ether and purified by Flash-chromatography. Yield 8.23%. 1H-NMR (400 MHz; CDCl3): δ 1.24 (d, 3H), 4.29 (dd, 1H), 4.41 (dd, 1H), 4.58 (m, 1H), 5.26 (s, 2H), 6.64 (d, 1H), 7.00 (t, 1H), 7.11 (t, 1H), 7.49 (d, 1H), 7.60 (s, 1H), 7.61 (d, 1H), 7.68 (d, 1H), 7.78 (dd, 1H), 8.08 (d, 1H), 8.17 (s, 1H).

Workup

  1. temperatureThe mixture was again cooled to 0° C.
  2. stirringThe reaction mixture was stirred overnight in RT
  3. customDMF was evaporated
  4. dissolutionthe resulting crude product was dissolved in DCM
  5. washwashed with brine
  6. customevaporated
  7. customThe product was triturated
  8. custompurified by Flash-chromatography

Sources & evidence

ORD record
ord-d23db6f0d6d84d9b972a12a925cf62b4
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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