3-Amino-5-methylpyridine → HCID 178430557, compound

HRID 2391010Notes

Reaction equation

HRID 2391010 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].[NH2:23][C:24]1[CH:25]=[N:26][CH:27]=[C:28]([CH3:30])[CH:29]=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:23][C:24]2[CH:25]=[N:26][CH:27]=[C:28]([CH3:30])[CH:29]=2)[CH2:9][CH2:8]1)=[O:5]

Participants

5

Reactant 3

HCID 27628943-Amino-5-methylpyridineHCID 5049666Sodium triacetoxyborohydrideHCID 178520978HCID 178520978, compound

Product 1

HCID 178430557HCID 178430557, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 50 mL round-bottomed flask containing trans-2-chloro-N-(4-formyl-cyclohexyl)-5-trifluoromethyl-benzamide (Ex. 1 step 3) (100 mg, 0.3 mmol) and 3-amino-5-methylpyridine (36 mg, 0.3 mmol) in dry DCM (5 mL) is added sodium triacetoxyborohydride (106 mg, 0.45 mmol) in one portion. The suspension is stirred at RT for 4 hours. The mixture is partitioned between DCM and saturated sodium bicarbonate, passed through a phase separator to recover the DCM layer and evaporated to give a colourless solid. The crude product is redissolved in DCM, absorbed directly onto silica gel and columned on silica gel using a 12 g pre-packed column and isohexane/EtOAc gradient elution (0% to 100% EtOAc). Product-containing fractions are combined and evaporated and the product is isolated as a colourless solid after trituration with 20% EtOAclisohexane, 55 mg, [MH+ 426.40].

Workup

  1. customThe mixture is partitioned between DCM and saturated sodium bicarbonate
  2. customto recover the DCM layer
  3. customevaporated
  4. customto give a colourless solid
  5. customabsorbed directly onto silica gel
  6. washa 12 g pre-packed column and isohexane/EtOAc gradient elution (0% to 100% EtOAc)
  7. customevaporated
  8. customthe product is isolated as a colourless solid after trituration with 20% EtOAclisohexane, 55 mg, [MH+ 426.40]

Sources & evidence

ORD record
ord-4669788e5ebc45b1aef857d64600b656
Source dataset
uspto-grants-2012_09
Patent number
US08273900B2

Reaction notes

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