Methylamine → HCID 86664020, compound

HRID 712306Notes

Reaction equation

HRID 712306 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([CH:16]=O)=[CH:14][C:13]([C:18]3[CH:19]=[N:20][C:21]([N:24]4[CH2:29][CH2:28][C:27]([CH3:35])([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:26][CH2:25]4)=[N:22][CH:23]=3)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].[CH3:36][NH2:37].[BH4-].[Na+]>C1COCC1.O>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([CH2:16][NH:37][CH3:36])=[CH:14][C:13]([C:18]3[CH:19]=[N:20][C:21]([N:24]4[CH2:29][CH2:28][C:27]([CH3:35])([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:26][CH2:25]4)=[N:22][CH:23]=3)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 86664021HCID 86664021, compound

Product 1

HCID 86664020HCID 86664020, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 1-[5-[2-(ethylcarbamoylamino)-7-formyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (140 mg, 0.28 mmol) was stirred in a 7M solution of methylamine in THF (8 mL) in a microwave tube equipped with a stirrer. The reaction was irradiated to 80° C. for 1 h in a CEM explorer microwave with stirring. After cooling, the solvents were removed under reduced pressure, the resulting residue dissolved in anhydrous MeOH (8 mL) and the reaction transferred to a round bottomed flask equipped with a calcium chloride drying tube. Sodium borohydride (43 mg, 1.12 mmol) was added and the reaction stirred at rt for 18 h. After this time LCMS indicated 70% conversion to the desired material. The reaction was diluted with water (20 mL), extracted with EtOAc (3×20 mL) and the combined organic extracts washed with brine, dried (MgSO4) and concentrated under reduced pressure to afford the crude product as a glassy brown/grey solid 130 mg (91% yield).

Workup

  1. customequipped with a stirrer
  2. customThe reaction was irradiated to 80° C. for 1 h in a CEM explorer microwave
  3. temperatureAfter cooling
  4. customthe solvents were removed under reduced pressure
  5. dissolutionthe resulting residue dissolved in anhydrous MeOH (8 mL)
  6. customthe reaction transferred to a round bottomed flask
  7. customequipped with a calcium chloride drying tube
  8. stirringthe reaction stirred at rt for 18 h
  9. extractionextracted with EtOAc (3×20 mL)
  10. washthe combined organic extracts washed with brine
  11. dry with materialdried (MgSO4)
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b28c4da73d0d432d961082d243c380c9
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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