Sodium triacetoxyborohydride → HCID 178523757, compound

HRID 2391016Notes

Reaction equation

HRID 2391016 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:3]=1[C:4]([NH:6][C@H:7]1[CH2:12][CH2:11][C@@H:10]([CH:13]=O)[CH2:9][CH2:8]1)=[O:5].[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:34]=[C:33]([NH2:35])[NH:32][N:31]=2)=[CH:26][CH:25]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:3]=1[C:4]([NH:6][C@H:7]1[CH2:12][CH2:11][C@@H:10]([CH2:13][NH:35][C:33]2[NH:32][N:31]=[C:30]([C:27]3[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=3)[CH:34]=2)[CH2:9][CH2:8]1)=[O:5]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 178507289HCID 178507289, compoundHCID 178520977HCID 178520977, compound

Product 1

HCID 178523757HCID 178523757, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Cis-2-Chloro-N-(4-formyl-cyclohexyl)-5-trifluoromethyl-benzamide (100 mg, 0.300 mmol) in DCM (3 mL) is added 3-(4-fluorophenyl)-1H-pyrazol-5-amine (58.4 mg, 0.330 mmol) to give a pale orange solution. This is stirred for 10 mins at room temperature before sodium triacetoxyborohydride (102 mg, 0.479 mmol) is added. The reaction mixture is stirred at room temperature for 1 hour. The reaction mixture is quenched by the addition of saturated sodium bicarbonate. The DCM layer is separated and further washed with water. The aqueous extracts are combined and re-extracted with DCM. The combined organic extracts are then dried over MgSO4, filtered and concentrated under vacuum. Purification by chromatography on a pre-packed 12 g silica gel column using 0-100% EtOAc in isohexane (gradient elution) gave the desired product as a colourless solid. [MH+495.29].

Workup

  1. customto give a pale orange solution
  2. additionis added
  3. customThe reaction mixture is quenched by the addition of saturated sodium bicarbonate
  4. customThe DCM layer is separated
  5. washfurther washed with water
  6. extractionre-extracted with DCM
  7. dry with materialThe combined organic extracts are then dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customPurification by chromatography on a pre-packed 12 g silica gel column

Sources & evidence

ORD record
ord-aa790daa6972467d8a62907f592ec637
Source dataset
uspto-grants-2012_09
Patent number
US08273900B2

Reaction notes

Loading…