Methylamine → HCID 57807979, compound

HRID 730308Notes

Reaction equation

HRID 730308 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([NH:11][C:12]3[CH:17]=[C:16]([C:18]4[CH:23]=[CH:22][C:21]([C:24](=[O:26])[CH3:25])=[CH:20][CH:19]=4)[CH:15]=[CH:14][N:13]=3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.CN.[BH4-].[Na+]>CO>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([NH:11][C:12]3[CH:17]=[C:16]([C:18]4[CH:23]=[CH:22][C:21]([CH:24]([OH:26])[CH3:25])=[CH:20][CH:19]=4)[CH:15]=[CH:14][N:13]=3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 57808205HCID 57808205, compound

Product 1

HCID 57807979HCID 57807979, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To the suspension of 1-{4-[2-(2,3-dihydro-benzo[1,4]dioxin-6-ylamino)-pyridin-4-yl]-phenyl}-ethanone (Example 7, 0.19 g, 0.55 mmol) in 2 mL of MeOH was added a solution of methylamine in MeOH (Aldrich Chemical Company) (2N, 0.55 mL, 1.1 mmol). The reaction was stirred at room temperature under nitrogen overnight. NaBH4 (Aldrich Chemical Company) (25 mg, 0.66 mmol) was then added to the reaction and it was stirred for another 5 hrs. The solvent was evaporated the residue was purified on a Biotage 40M column (97:3 dichloromethane:2N NH3 in MeOH) to give the title compound as an off-white foam. MS (ESI, pos. ion) m/z: 349 (M+1). Mp: 55.9-61.5° C.

Workup

  1. stirringwas stirred for another 5 hrs
  2. customThe solvent was evaporated the residue
  3. customwas purified on a Biotage 40M column (97:3 dichloromethane:2N NH3 in MeOH)

Sources & evidence

ORD record
ord-d56344fae4934b42996fe9e825f86534
Source dataset
uspto-grants-2009_09
Patent number
US07582657B2

Reaction notes

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